1-1-diphenyl-2-picrylhydrazyl and vanillin

A number of novel naphthalimido and phthalimido vanillin derivatives were synthesised, and evaluated as antioxidants and cholinesterase inhibitors in vitro. Antioxidant activity was assessed using DPPH, FRAP, and ORAC assays. All compounds demonstrated enhanced activity compared to the parent compound, vanillin. They also exhibited BuChE selectivity in Ellman's assay. A lead compound, 2a (2-(3-(bis(4-hydroxy-3-methoxybenzyl)amino)propyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione), was identified and displayed strong antioxidant activity (IC

Topics: Acetylcholinesterase; Alzheimer Disease; Antioxidants; Benzaldehydes; Biphenyl Compounds; Butyrylcholinesterase; Cholinesterase Inhibitors; Dose-Response Relationship, Drug; Humans; Models, Molecular; Molecular Structure; Neuroprotective Agents; Picrates; Structure-Activity Relationship

The present study aimed to explore the ability of vanillin to ameliorate the adverse effects induced by potassium bromate (KBrO3) in the renal tissue. Our results showed a significant increase in hydrogen peroxide, superoxide anion, malondialdehyde, advanced oxidation protein product and protein carbonyl levels in the kidney of KBrO3 treated mice, compared with the control group. Nephrotoxicity was evidenced by a decrease in plasma uric acid and kidney glutathione levels, Na(+)-K(+)-ATPase, lactate dehydrogenase and catalase activities. Additionally, creatinine and urea levels significantly increased in the plasma and declined in the urine. Also, Kidney glutathione peroxidase, superoxide dismutase, metallothionein (MT1 and MT2) mRNA expression remarkably increased. These modifications in biochemical and molecular values were substantiated by histopathological data. Co-treatment with vanillin restored these parameters to near control values. Interestingly, vanillin proved to possess, in vitro, a stronger scavenging radical activity than vitamin C and Trolox. Thus, vanillin inhibited KBrO3-induced damage via its antioxidant and antiradical activities as well as its capacity to protect genes expression and histopathological changes.

Topics: Adenosine Triphosphatases; Animals; Antioxidants; Benzaldehydes; Benzothiazoles; Biphenyl Compounds; Bromates; Environmental Pollutants; Hair Preparations; Kidney; Lipid Peroxidation; Metallothionein; Mice; Oxidative Stress; Picrates; Sulfonic Acids; Up-Regulation

Antioxidant activity of a number of small (low molecular weight) natural compounds found in spices, condiments or drugs (gallic acid, sesamol, eugenol, thymol, carvacrol, vanillin, salicylaldehyde, limonene, geraniol, 4-hexylresorcinol, etc.) has been evaluated using electrochemical and DPPH• radical scavenging measurements. Structural analysis of the tested compound suggest a remarkable activity for phenol derivatives and the importance of the -R groups located on the phenolic ring in the molecule's ability to act as free radical scavenging as well as their influence in the electrochemical behavior. The voltammetric method can be used for the determination of the antioxidant capability in the same manner as the DPPH• radical scavenging because of the correlation found between oxidation potentials and anti-radical power (ARP = 1/EC₅₀). Such electrochemical determination is fast and cheap and allows making measurements under a variety of experimental conditions. The accuracy of the electrochemical measurements is the same for all the compounds, irrespective of their scavenging activity, the opposite of what occurs in the DPPH• test.

Topics: Acyclic Monoterpenes; Aldehydes; Antioxidants; Benzaldehydes; Benzodioxoles; Biphenyl Compounds; Condiments; Cyclohexenes; Cymenes; Electrochemical Techniques; Eugenol; Free Radicals; Gallic Acid; Hexanes; Hexylresorcinol; Limonene; Monoterpenes; Oxidation-Reduction; Phenols; Picrates; Prescription Drugs; Resorcinols; Spices; Terpenes; Thymol

Vanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, and antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent.. We systematically evaluated the antioxidant activity of vanillin using multiple assay systems. DPPH radical-, galvinoxyl radical-, and ABTS(+)-scavenging assays, ORAC assay and an oxidative hemolysis inhibition assay (OxHLIA) were used for determining the antioxidant activity.. Vanillin showed stronger activity than did ascorbic acid and Trolox in the ABTS(+)-scavenging assay but showed no activity in the DPPH radical- and galvinoxyl radical-scavenging assays. Vanillin showed much stronger antioxidant activity than did ascorbic acid and Trolox in the ORAC assay and OxHLIA. In the ABTS(+)-scavenging assay, ORAC assay and OxHLIA, vanillin reacted with radicals via a self-dimerization mechanism. The dimerization contributed to the high reaction stoichiometry against ABTS(+) and AAPH-derived radicals to result in the strong effect of vanillin. Oral administration of vanillin to mice increased the vanillin concentration and the antioxidant activity in plasma. These data suggested that antioxidant activity of vanillin might be more beneficial than has been thought for daily health care.. Based on the results of the present study, we propose the addition of antioxidant capacity to the multifunctionality of vanillin.

Topics: Animals; Antioxidants; Ascorbic Acid; Benzaldehydes; Benzhydryl Compounds; Benzothiazoles; Biphenyl Compounds; Chromans; Chromatography, High Pressure Liquid; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Erythrocytes; Free Radical Scavengers; Hemolysis; Mice; Molecular Structure; Oxidation-Reduction; Picrates; Sheep; Sulfonic Acids

A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expressed as IC50 value. Compounds 2c, 2d, 4d, and 6a showed appreciable radical scavenging activities. The vanillin based thiazolidinedione compound 2c displayed highest activity comparable to that of alpha-tocopherol. But in vivo, compound 6a showed better results in inducing phase II detoxifying/antioxidative enzyme.

Topics: alpha-Tocopherol; Antioxidants; Benzaldehydes; Biphenyl Compounds; Free Radical Scavengers; Inhibitory Concentration 50; Picrates; Protein Prenylation; Structure-Activity Relationship; Thiazolidinediones

Vanilla extract was prepared by extraction of cured vanilla beans with aqueous ethyl alcohol (60%). The extract was profiled by HPLC, wherein major compounds, viz., vanillic acid, 4-hydroxybenzyl alcohol, 4-hydroxy-3-methoxybenzyl alcohol, 4-hydroxybenzaldehyde and vanillin, could be identified and separated. Extract and pure standard compounds were screened for antioxidant activity using beta-carotene-linoleate and DPPH in vitro model systems. At a concentration of 200 ppm, the extract showed 26% and 43% of antioxidant activity by beta-carotene-linoleate and DPPH methods, respectively, in comparison to corresponding values of 93% and 92% for BHA. Interestingly, 4-hydroxy-3-methoxybenzyl alcohol and 4-hydroxybenzyl alcohol exhibited antioxidant activity of 65% and 45% by beta-carotene-linoleate method and 90% and 50% by DPPH methods, respectively. In contrast, pure vanillin exhibited much lower antioxidant activity. The present study points toward the potential use of vanilla extract components as antioxidants for food preservation and in health supplements as nutraceuticals.

Topics: Antioxidants; Benzaldehydes; beta Carotene; Biphenyl Compounds; Chromatography, High Pressure Liquid; Linoleic Acid; Picrates; Plant Extracts; Seeds; Vanilla

Vanillin, a plant derived natural product, used as food flavoring agent and its positional isomer o-vanillin, have been tested for their ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical using high performance liquid chromatography (HPLC). Trolox, a water-soluble analogue of vitamin E and a well-known antioxidant was used as a reference compound. The DPPH radical was monitored at 517 nm and its retention time was 8.6 min. From the decrease in optical density of DPPH radical in the presence of the test compounds, it was observed that o-vanillin was a more effective scavenger than vanillin. At equimolar concentrations (1 mM), vanillin and o-vanillin exhibited 22.9% and 66.4% DPPH radical scavenging activity, respectively. The kinetics of the reaction of vanillin and o-vanillin with DPPH radical was studied using stopped flow spectrophotometry and their rate constants were estimated to be 1.7 +/- 0.1 M(-1)s(-1) and 10.1 +/- 0.8 M(-1)s(-1), respectively. In comparison, the rate constant for the reaction of trolox with DPPH was estimated to be 360.2 +/- 10.1 M(-1)s(-1). These scavenging reactions involve electron/H-atom transfer from antioxidant to DPPH. To confirm this, one electron reduction potentials of these compounds were estimated using cyclic voltammetry which showed that o-vanillin was more easily oxidized than vanillin. The reduction potential for o-vanillin was about 1.5 times that of trolox. These results demonstrate that o-vanillin is a more potent antioxidant than vanillin.

Topics: Antioxidants; Benzaldehydes; Biophysical Phenomena; Biophysics; Biphenyl Compounds; Chromans; Chromatography, High Pressure Liquid; Dose-Response Relationship, Drug; Free Radical Scavengers; Indicators and Reagents; Kinetics; Oxygen; Picrates; Time Factors