1-1-diphenyl-2-picrylhydrazyl and ferulic-acid

Ferulic acid (FA) is an effective chemopreventive and therapeutic agent for colorectal cancer. However, FA cannot stably reach the colon through human digestive system, and it can be grafted into oligosaccharides to improve its digestion stability. Therefore, in this study, different degrees of substitution of feruloylated oat β-glucan (FA-OβG) were prepared by grafting FA onto water soluble oat β-glucan. FA grafting changed the crystallinity and surface morphology of OβG, and the thermal stability of the FA-OβG improved. As the DS increased, the antioxidant activity of FA-OβG increased, and FA-OβG III with DS of 0.184 showed the same antioxidant activities compared to the equal amount of free FA. The FA-OβG showed higher stability under gastrointestinal and colonic conditions than free FA. Furthermore, the FA-OβG conjugates exhibited good in vitro anticancer activity against human colorectal cancer cells, while FA-OβG III showed better anticancer activity than an equal amount of free FA.

Topics: Adult; Antineoplastic Agents, Phytogenic; Antioxidants; Benzothiazoles; beta-Glucans; Biphenyl Compounds; Cell Proliferation; Colon; Coumaric Acids; Feces; Female; Fermentation; Gastric Juice; HCT116 Cells; Humans; Intestinal Secretions; Male; Picrates; Sulfonic Acids; Surface Properties; Young Adult

Topics: Acetylcholinesterase; Alzheimer Disease; Animals; Antioxidants; Biological Products; Biphenyl Compounds; Butyrylcholinesterase; Cholinesterase Inhibitors; Coumaric Acids; Dose-Response Relationship, Drug; Horses; Humans; Models, Molecular; Molecular Structure; Neuroprotective Agents; Picrates; Piperazine; Structure-Activity Relationship

Insulin resistance is a major pathophysiological feature in the development of type 2 diabetes (T2DM). Ferulic acid is known for attenuating the insulin resistance and reducing the blood glucose in T2DM rats. In this work, we designed and synthesized a library of new ferulic acid amides (FAA), which could be considered as ring opening derivatives of the antidiabetic PPARγ agonists Thiazolidinediones (TZDs). However, since these compounds displayed weak PPAR transactivation capacity, we employed a proteomics approach to unravel their molecular target(s) and identified the peroxiredoxin 1 (PRDX1) as a direct binding target of FAAs. Interestingly, PRDX1, a protein with antioxidant and chaperone activity, has been implied in the development of T2DM by inducing hepatic insulin resistance. SPR, mass spectrometry-based studies, docking experiments and in vitro inhibition assay confirmed that compounds VIe and VIf bound PRDX1 and induced a dose-dependent inhibition. Furthermore, VIe and VIf significantly improved hyperglycemia and hyperlipidemia in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats as confirmed by histopathological examinations. These results provide guidance for developing the current FAAs as new potential antidiabetic agents.

Topics: Amides; Animals; Biphenyl Compounds; Cell Survival; Coumaric Acids; Diabetes Mellitus, Experimental; Dose-Response Relationship, Drug; Enzyme Inhibitors; Humans; Hypoglycemia; Hypoglycemic Agents; Hypolipidemic Agents; Male; Models, Molecular; Molecular Structure; Peroxiredoxins; Picrates; Rats; Rats, Sprague-Dawley; Rats, Wistar; Streptozocin; Structure-Activity Relationship; Tumor Cells, Cultured

Topics: Anions; Antioxidants; Arabinose; Benzothiazoles; Biological Availability; Biphenyl Compounds; Cations; Coumaric Acids; Dietary Fiber; Flavonoids; Fruit; Galactose; Glucose; Hydroxybenzoates; Mannose; Micronutrients; Minerals; Opuntia; Pectins; Picrates; Plant Mucilage; Polyphenols; Polysaccharides; Rhamnose; Sulfonic Acids; Xylose

The DPPH (2,2-Diphenyl-1-picrylhydrazyl) assay is an easy and efficient method commonly used to determine the antioxidant capacity of many food matrices and beverages. In contrast with red wines, white wines are poorer in antioxidant polyphenolics, and the more hydrophilic sulfur-containing compounds in them may contribute significantly to their antioxidant capacity. The modification of the classical DPPH method, with a methanol-buffer and the measure of EC

Topics: Antioxidants; Biphenyl Compounds; Caffeic Acids; Catechin; Coumaric Acids; High-Throughput Screening Assays; Humans; Phenols; Picrates; Sulfur Compounds; Wine

Topics: Antioxidants; Avena; Bile Acids and Salts; Biphenyl Compounds; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Coumaric Acids; Flour; Pentoses; Picrates; Polysaccharides; Rheology; Solubility; Water

Diabetes complications, including peripheral neuropathy, cataracts, impaired wound healing, vascular damage, arterial wall stiffening and retinopathy diseases, are among the most predominant health problems facing the world's population today. The 22 Peruvian plant extracts were screened for their potential inhibitory activity against rat lens aldose reductase (RLAR) and DPPH radical scavenging. Among them, we have found that

Topics: Aldehyde Reductase; Animals; Apigenin; Biphenyl Compounds; Chromatography, High Pressure Liquid; Coumaric Acids; Flavones; Glucosides; Kaempferols; Luteolin; Picrates; Plants, Medicinal; Rats; Sorbitol; Tanacetum parthenium

In this study, four main components of feruloylated oligosaccharides (FOs),FOs-1, FOs-2, FOs-3 and FOs-4,were isolated from wheat bran by use of Amberlite XAD-2 and Sephadex LH-20. Structural characterization of FOs was determined by use of high performance liquid chromatography (HPLC), gas chromatography (GC) and fourier transform-infrared spectroscopy (FT-IR). Antioxidant properties were investigated in vitro. Average degrees of polymerization (DP) of the four components (FOs-1, FOs-2, FOs-3 and FOs-4) were approximately 10.6, 7.7, 6.1 and 3.4, respectively. In addition, DP were consistent with molar ratios of arabinose and xylose in 1:9.46, 1:5.30, 1:2.91 and 1:0.19, respectively. The presence of β-glycosidic linkage was confirmed at 896 cm - 1 by use of FT-IR. In vitro antioxidant studies demonstrated that FOs-1, FOs-2, FOs-3 and FOs-4 possessed significant antioxidant activities in the dose-dependent manner. In addition, the degree of polymerization affected antioxidant capacity. These results have improved our understanding of the relationship between FOs with different structural types and their antioxidant activities.

Topics: Antioxidants; Biphenyl Compounds; Chelating Agents; Chromatography, High Pressure Liquid; Coumaric Acids; Dietary Fiber; Free Radical Scavengers; Hydroxyl Radical; Ions; Metals; Oligosaccharides; Picrates; Polymerization; Reference Standards; Spectroscopy, Fourier Transform Infrared; Superoxides

The antiradical efficiency (AE) and kinetic behavior of a new ferulate-based protic ionic liquids (PILs) were described using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay. The reduction of the DPPH free radical (DPPH•) was investigated by measuring the decrease in absorbance at 517 nm. The time to reach steady state for the reaction of parent acid (ferulic acid) and synthesized PILs with DPPH• was continuously recorded for 1 h. Results revealed that the AE of 2-butylaminoethanol ferulate (2BAEF), 3-dimethylaminopropanol ferulate (3DMAPF) and 3-diethylaminopropanol ferulate (3DEAPF) PILs have improved compared to ferulic acid (FA) as the reaction class changes from low to medium. This attributed to the strong hydrogen abstraction occurred in the PILs. Furthermore, these PILs were found to have a good kinetic behavior compared to FA due to the high rate constant (

Topics: Biological Assay; Biphenyl Compounds; Coumaric Acids; Dose-Response Relationship, Drug; Free Radical Scavengers; Ionic Liquids; Kinetics; Molecular Structure; Picrates

The diet supplementation with antioxidants-rich products is a way to protect people from free radical-induced diseases. In this study, we compare the anti-inflammatory/antioxidant activity of two compounds available as supplements: alpha lipoic acid (ALA) and ferulic acid (FA).. The free radical scavenging capacity of ALA and FA in the cell free system was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Anti-inflammatory activity of both compounds was determined, in vitro, on THP-1 derived macrophages model, both resting (not stimulated) and inflammatory (lipopolysaccharide- or tumor-necrosis factor α-stimulated).. We have found that FA exhibits much higher radical scavenging activity than ALA, in cell free system. The functional assays demonstrated that although both ALA and FA limited the reactive oxygen species (ROS) formation in the presence of inflammatory macrophages, the latter acid was significantly more effective. Only FA reduced the release of pro-inflammatory interleukin 1β and interleukin 6 by lipopolysaccharide-treated macrophages. Neither FA nor ALA affected the viability of macrophages.. Among those two compounds only FA has significant free radical scavenging activity in cell free system and acts as anti-inflammatory and antioxidant agent on macrophages. It can be assumed that application of FA in a diet can protect the host from the development and/or progression of inflammation.

Topics: Anti-Inflammatory Agents; Antioxidants; Biphenyl Compounds; Cell Line; Coumaric Acids; Free Radical Scavengers; Humans; Inflammation; Interleukin-1beta; Interleukin-6; Lipopolysaccharides; Macrophages; Oxidants; Picrates; Reactive Oxygen Species; Thioctic Acid; Tumor Necrosis Factor-alpha

In this study, a series of novel ferulic and caffeic acid dimers was designed and synthesised, and their multifunctional properties against Alzheimer's disease (AD) were evaluated. Results showed that our multifunctional strategy was great supported by enhancing the inhibition of Aβ

Topics: Alzheimer Disease; Amyloid beta-Peptides; Animals; Antioxidants; Biphenyl Compounds; Caffeic Acids; Cell Death; Cell Line; Coumaric Acids; Free Radical Scavengers; Glutamic Acid; Humans; Mice; Neurons; Peptide Fragments; Picrates

The current study is focused on optimizing the parameters involved in enzymatic processing of red rice bran for maximizing total polyphenol (TP) and free radical scavenging activity (FRSA). The sequential optimization strategies using central composite design (CCD) and artificial neural network (ANN) modeling linked with genetic algorithm (GA) was performed to study the effect of incubation time (60-90 min), xylanase concentration (5-10 mg/g), cellulase concentration (5-10 mg/g) on the response, i.e., total polyphenol and FRSA. The result showed that incubation time has a negative effect on the response, while the square effect of xylanase and cellulase showed positive effect on the response. A maximum TP of 2,761 mg ferulic acid Eq/100 g bran and FRSA of 778.4 mg Catechin Eq/100 g bran was achieved with incubation time (min) = 60.491; xylanase (mg/g) = 5.4633; cellulase (mg/g) = 11.5825. Furthermore, ANN-GA-based optimization showed better predicting capabilities as compared to CCD.

Topics: Aspergillus niger; Biphenyl Compounds; Cellulase; Coumaric Acids; Endo-1,4-beta Xylanases; Free Radical Scavengers; Free Radicals; Neural Networks, Computer; Oryza; Picrates; Plant Extracts; Polyphenols

The present study was aimed to evaluate the radioprotective effect of ferulic acid (FA), a naturally occurring plant flavonoid in terms of DNA damage and damage related alterations of repair pathways by gamma radiation. FA was administered at a dose of 50 mg/kg body weight for five consecutive days prior to exposing the swiss albino mice to a single dose of 10 Gy gamma radiation. Ionising radiation induces oxidative damage manifested by decreased expression of Cu, Zn-SOD (SOD stands for super oxide dismutase), Mn-SOD and catalase. Gamma radiation promulgated reactive oxygen species (ROS) mediated DNA damage and modified repair pathways. ROS enhanced nuclear translocation of p53, activated ATM (ataxia telangiectasia-mutated protein), increased expression of GADD45a (growth arrest and DNA-damage-inducible protein) gene and inactivated Non homologous end joining (NHEJ) repair pathway. The comet formation in irradiated mice peripheral blood mononuclear cells (PBMC) reiterated the DNA damage in IR exposed groups. FA pretreatment significantly prevented the comet formation and regulated the nuclear translocation of p53, inhibited ATM activation and expression of GADD45a gene. FA promoted the nuclear translocation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) and activated NHEJ repair pathway to overcome ROS mediated oxidative stress and DNA damage. Therefore, the current study stated that FA can challenge the oxidative stress by (i) inducing nuclear translocation of Nrf2, (ii) scavenging ROS, and (iii) activating NHEJ DNA repair process.

Topics: Animals; Biphenyl Compounds; Catalase; Composite Resins; Coumaric Acids; DNA Damage; DNA End-Joining Repair; Drug Evaluation, Preclinical; Free Radical Scavengers; Gamma Rays; Male; Mice; NF-E2-Related Factor 2; Oxidation-Reduction; Oxidative Stress; Picrates; Plasmids; Radiation-Protective Agents; Signal Transduction; Superoxide Dismutase; Transcriptional Activation

Persistent accumulation of reactive oxygen species causes cellular oxidative stress which contributes strongly towards the induction and progression of various diseases. Therapeutic focus has therefore shifted towards the use of antioxidants, with recent interest in those of plant origin. In the current study, rosmarinic acid (RA) and its key metabolites were evaluated in non-cellular and cellular antioxidant assays, using quercetin (Q) as a positive control. The non-cellular assay was performed as scavenging of DPPH radical, whilst the cellular assay was performed as protection from an oxidant stress. Radical-scavenging activity of RA and two of its primary metabolites, CA and DHPLA, were comparable to that of Q, whilst FA was of lower potency and m-CoA was inactive. In the cellular assay, RA and CA were markedly less potent than Q, with DHPLA, FA and m-CoA being inactive, this being true in short-term (5-h) or long-term (20-h) exposure conditions. However, antioxidant potency of Q and methyl rosmarinate, a non-ionisable ester of RA, was similar in the non-cellular and short-term cellular assays. It is proposed that marked ionisation of organic acids such as RA and its metabolites at physiological pH greatly limits their intracellular accumulation, and so attenuates intrinsic antioxidant ability demonstrated in the non-cellular assay. This study demonstrates some of the factors that prevent well-known phytochemicals from progressing further along the drug discovery chain.

Topics: Antioxidants; Biphenyl Compounds; Caffeic Acids; Cinnamates; Coumaric Acids; Depsides; Hep G2 Cells; Humans; Hydrogen-Ion Concentration; Oxidative Stress; Picrates; Quercetin; Rosmarinic Acid

Steryl ferulates (SFs) are a subclass of bioactive lipids contributing to the health-promoting effects of whole grains. Most related studies focus on γ-oryzanol, a SF mixture from rice, since individual steryl ferulates are not commercially available. There is little evidence that individual SFs may vary in their bioactivity. The aim of this study was to evaluate the antioxidant activity of eight individual SFs by determining their radical scavenging capacity. Additional molecular properties of the individual SFs were determined by molecular simulation in order to identify correlations with their antioxidant activities. Our study demonstrates that individual SFs exhibit 1,1-diphenyl-2-picrylhydrazyl radical, hydroxyl radical, and superoxide anion radical scavenging abilities with subtle differences that were highly dependent on the kind of reaction taking place. The grouping of SFs by principle component analysis was mainly attributed to molecular properties, not antioxidant activities. Solvation energy was significantly correlated with some experimental observations. To our knowledge, this is the first study to evaluate the antioxidant activity of eight individual steryl ferulates from different sources. Results of this work will provide better insight into the antioxidant activity of SFs and the health benefits of whole grains.

Topics: Algorithms; Antioxidants; Biphenyl Compounds; Coumaric Acids; Dietary Fiber; Edible Grain; Electron Spin Resonance Spectroscopy; Molecular Structure; Oryza; Oxidation-Reduction; Phenylpropionates; Phytosterols; Picrates; Plant Extracts

In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9μM) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture.

Topics: Acetylcholinesterase; Amino Acid Motifs; Amyloid beta-Peptides; Animals; Antioxidants; Binding Sites; Biphenyl Compounds; Carbazoles; Cholinesterase Inhibitors; Coumaric Acids; Drug Design; Electrophorus; Galantamine; Hydrogen Peroxide; Molecular Docking Simulation; Molecular Sequence Data; Neuroprotective Agents; PC12 Cells; Peptide Fragments; Picrates; Protein Binding; Rats; Structure-Activity Relationship

Hydroxycinnamic acid bound arabinoxylans (HCA-AXs) were extracted from brans of five Indian millet varieties and response surface methodology was used to optimize the extraction conditions. The optimal condition to obtain highest yield of millet HCA-AXs was determined as follows: time 61min, temperature 66°C, ratio of solvent to sample 12ml/g. Linkage analysis indicated that hydroxycinnamic acid bound arabinoxylan from kodo millet (KM-HCA-AX) contained comparatively low branched arabinoxylan consisting of 14.6% mono-substituted, 1.2% di-substituted and 41.2% un-substituted Xylp residues. The HPLC analysis of millet HCA-AXs showed significant variation in the content of three major bound hydroxycinnamic acids (caffeic, p-coumaric and ferulic acid). The antioxidant activity of millet HCA-AXs were evaluated using three in vitro assay methods (DPPH, FRAP and β-carotene linoleate emulsion assays) which suggested both phenolic acid composition and structural characteristics of arabinoxylans could be correlated to their antioxidant potential, the detailed structural analysis revealed that low substituted KM-HCA-AX exhibited relatively higher antioxidant activity compared to other medium and highly substituted HCA-AXs from finger (FM), proso (PM), barnyard (BM) and foxtail (FOXM) millet.

Topics: Antioxidants; beta Carotene; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Dietary Fiber; Factor Analysis, Statistical; Fluorescence Recovery After Photobleaching; Millets; Picrates; Propionates; Solid Phase Extraction; Structure-Activity Relationship; Temperature; Time Factors; Xylans

The aim of the present research was to study the thermal stability of ferulic acid after coupling onto chitosan, and the possibility of using ferulic acid-coupled chitosan (FA-CTS) as an antioxidant for biodegradable active packaging film. FA-CTS was incorporated into biodegradable film via a two-step process, i.e. compounding extrusion at temperatures up to 150°C followed by blown film extrusion at temperatures up to 175°C. Although incorporation of FA-CTS with a content of 0.02-0.16% (w/w) caused decreased water vapor barrier property and reduced extensibility, the biodegradable films possessed improved oxygen barrier property and antioxidant activity. Radical scavenging activity and reducing power of film containing FA-CTS were higher than those of film containing naked ferulic acid, by about 254% and 94%, respectively. Tensile strength and rigidity of the films were not significantly affected by the addition of FA-CTS with a content of 0.02-0.08% (w/w). The above results suggested that FA-CTS could potentially be used as an antioxidant for active packaging film.

Topics: Antioxidants; Biphenyl Compounds; Chitosan; Coumaric Acids; Food Packaging; Glycerol; Hot Temperature; Lactic Acid; Oxygen; Picrates; Polyesters; Polymers; Starch; Tensile Strength; Water; X-Ray Diffraction

Essential oils have played a prominent role in research on natural products, due to the high level of bioactive constituents, which include those derived from phenylpropanoids or terpenoids. This study aimed to evaluate the antioxidant capacity of isopentyl ferulate (IF) employing in vitro experimental models for elimination of the 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS+), hydroxyl (OH) and nitric oxide (NO), as well as its capacity to electron transfer by reducing potential and inhibition of lipid peroxidation by TBARS (thiobarbituric acid reactive substances) method. In all in vitro antioxidants protocols, isopentyl ferulate showed to be potent in a concentration of 54.4 nM, presenting a percentage inhibition of 91.29±0.57, 92.63±0.28, 83.62±0.18, 77.07±0.72 and 79.51±0.32% for DPPH, ABTS+, hydroxyl, nitric oxide and TBARS level, respectively. The increase of absorbance at 700 nm in the concentrations of 3.4, 6.8, 13.6, 27.2 and 54.4 nM shows the reducing potential of IF. Similar results were obtained with Trolox (559 nM), a hydrophilic synthetic analogue of α-tocopherol, which is widely used as a standard antioxidant. The present study demonstrated that isopentyl ferulate has an antioxidant activity in vitro experimental models, suggesting that this compound could enhance the development of a new product with antioxidant properties. However, further in vivo studies are needed to assign possible implications in the treatment of diseases related with free radicals.

Topics: Benzothiazoles; Biphenyl Compounds; Coumaric Acids; Free Radical Scavengers; Hydroxyl Radical; Nitric Oxide; Oxidation-Reduction; Picrates; Sulfonic Acids; Thiobarbituric Acid Reactive Substances

Black rice bran contains phenolic compounds of a high antioxidant activity. In this study, the 40% acetone extract of black rice bran was sequentially fractionated to obtain 5 fractions. Out of the 5 fractions, ethyl acetate fraction was subfractionated using the Sephadex LH-20 chromatography. The antioxidant activity of phenolic compounds in the extracts was investigated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay, 2,2-azino-bis-(3-ethylenebenzothiozoline-6-sulfonic acid) (ABTS) radical cation assay, reducing power. The subfraction 2 from ethyl acetate fraction had the highest total phenolic contents (TPC) (816.0 μg/mg) and the lowest EC50 values (47.8 μg/mL for DPPH radical assay, 112.8 μg/mL for ABTS radical cation assay, and 49.2 μg/mL for reducing power). These results were 3.1, 1.3, and 2.6 times lower than those of butylated hydroxytoluene (BHT), respectively. At a concentration of 100 μg/mL, the antioxidant activity and TPC of various extracts was closely correlated, with correlation coefficients (R(2) ) higher than 0.86. The major phenolic acid in subfraction 2 was identified as ferulic acid (178.3 μg/mg) by HPLC and LC-ESI/MS/MS analyses. Our finding identified ferulic acid as a major phenolic compound in black rice bran, and supports the potential use of black rice bran as a natural source of antioxidant.

Topics: Antioxidants; Benzothiazoles; Biphenyl Compounds; Chromatography; Chromatography, High Pressure Liquid; Coumaric Acids; Dextrans; Hydroxybenzoates; Indicators and Reagents; Oryza; Phenols; Picrates; Plant Extracts; Sulfonic Acids; Tandem Mass Spectrometry

The complexes formed by two polyphenols, trans-Ferulic acid (FA) and Gallic acid (GA) with 2-hydroxypropyl-b-cyclodextrin (HPβCD), by the spray-drying method, were studied. Encapsulation-efficiencies (EE) of the complexes prepared were evaluated by HPLC. In the case of co-encapsulation, the EE of GA was lowered, whereas that of FA was almost stable, indicating a possible antagonistic relationship between the two phenols for the HPβCD cavity. The physicochemical characterization of the complexes was carried out by Fourier Transform Infrared Spectroscopy (FT-IR), Differential Scanning Calorimetry (DSC), and Scanning Electron Microscopy (SEM). SEM observations revealed that the coencapsulated phenolic complex resulted in a more rounded shape outer surfaces of HPβCD than when encapsulated separately. FT-IR and DSC data indicated that the two polyphenols exhibit a possible interaction in the coencapsulated complex. The complexes showed no loss of their ability to scavenge DPPH radical relatively to the single agent at the concentrations used.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Biphenyl Compounds; Calorimetry, Differential Scanning; Chemical Phenomena; Coumaric Acids; Drug Compounding; Gallic Acid; Microscopy, Electron, Scanning; Picrates; Spectroscopy, Fourier Transform Infrared

A comparative analysis of ethanol extracts from peel, pulp and seed of Prunus persica var. platycarpa (Tabacchiera peach) was done. The total phenol, flavonoid and carotenoid content as well as the antioxidant properties by using different in vitro assays (DPPH, ABTS, FRAP, Fe-chelating, β-carotene bleaching test) were evaluated. Pulp extract was subjected to liquid chromatography-electrospray-tandem mass spectrometry (HPLC-ESI-MS/MS). Gallic acid, protocatechuic acid, protocatechualdehyde, chlorogenic acid, p-coumaric acid, and ferulic acid were identified as main constituents. Pulp extract was characterized by the highest total phytonutrients content and exhibited the highest antioxidant activity in all in vitro assays (IC(50) values of 2.2 μg/mL after 60 min of incubation by using β-carotene bleaching test and 2.9 μg/mL by using Fe-chelating assay). Overall, the obtained results suggest that P. persica var. platycarpa displays a good antioxidant activity and its consumption could be promoted.

Topics: Antioxidants; Benzaldehydes; Benzothiazoles; beta Carotene; Biphenyl Compounds; Catechols; Chlorogenic Acid; Chromatography, High Pressure Liquid; Coumaric Acids; Fruit; Gallic Acid; Humans; Hydroxybenzoates; Oxidation-Reduction; Picrates; Plant Extracts; Propionates; Prunus persica; Seeds; Species Specificity; Sulfonic Acids; Tandem Mass Spectrometry

Roscoea purpurea (Zingiberaceae) is commonly known as "kakoli". Traditionally, various parts like leaves, roots and flower etc. are used for the treatment of diabetic, hypertension, diarrhea, fever, inflammation etc. In Nepal tubers are boiled for edible purpose and also used in traditional veterinary medicine. The study aims for nutritional characterization, chemical profiling of R. purpurea (tubers) methanol extract (RPE) along with evaluation of its anti-oxidant activity. Physicochemical and nutritional content were estimated as per standard protocols. Chemical profiling of markers includes method optimization, identification & quantification of bioactive poly phenolics through HPTLC. Anti oxidant potential RPE was analyzed via. Total phenolics (TPC), total flavonoids (TFC), reducing power assay, DPPH and β-carotene bleaching model.. Physicochemical and nutritional standards were established. Kaempferol (0.30%), vanillic acid (0.27%), protocatechuic (0.14%), syringic (0.80%) and ferulic acid (0.05%) were identified and then quantified. TPC and TFC content were found to be 7.10 ± 0.115 and 6.10 ± 0.055%, reducing power of extract also increases linearly (r(2) = 0.946) with concentration, similar to standards. IC50 value of extract in DPPH and β-carotene bleaching model was observed at 810.66 ± 1.154 and 600.66 ± 1.154 µg/ml, which is significantly different from standards (p < 0.05). Although there is a positive, significant correlation between the phenolic and flavonoid content with anti oxidant activity of extract.. Thus, study will authenticates the identity, utility of herb as nutrient supplement and an important medicinal plant having promising pharmacological activities for further elaborated/extended investigation work.

Topics: Antioxidants; beta Carotene; Biphenyl Compounds; Chromatography, High Pressure Liquid; Coumaric Acids; Hydroxybenzoates; Kaempferols; Phenols; Picrates; Plant Extracts; Plant Tubers; Vanillic Acid; Zingiberaceae

In this study, firstly, antioxidant and polyphenol oxidase (PPO) properties of Yomra apple were investigated. Seventeen phenolic constituents were measured by reverse phase-high-performance liquid chromatography (RP-HPLC). Total phenolic compounds (TPCs), ferric reducing antioxidant power (FRAP) and 2, 2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging activities were performed to measure antioxidant capacity. Some kinetic parameters (Km, Vmax), and inhibition behaviors against five different substrates were measured in the crude extract. Catechin and chlorogenic acid were found as the major components in the methanolic extract, while ferulic acid, caffeic acid, p-hydroxybenzoic acid, quercetin and p-coumaric acid were small quantities. Km values ranged from 0.70 to 10.10 mM in the substrates, and also 3-(4-hydroxyphenyl) propanoic acid (HPPA) and L-DOPA showed the highest affinity. The inhibition constant of Ki were ranged from 0.05 to 14.90 mM against sodium metabisulphite, ascorbic acid, sodium azide and benzoic acid, while ascorbic acid and sodium metabisulphite were the best inhibitors.

Topics: Antioxidants; Ascorbic Acid; Biphenyl Compounds; Caffeic Acids; Catechin; Catechol Oxidase; Chlorogenic Acid; Coumaric Acids; Enzyme Inhibitors; Fruit; Kinetics; Levodopa; Malus; Oxidation-Reduction; Parabens; Phenylpropionates; Picrates; Plant Extracts; Plant Proteins; Polyphenols; Propionates; Quercetin; Sulfites

Various hydroxycinnamoyl β-d-xylopyranosides were efficiently prepared from 2,3,4-tri-O-acetyl-α-d-xylopyranosyl bromide (TAXB) with amine by amine-promoted glycosylation. The resulted acetylated hydroxycinnamoyl β-d-xylopyranosides with acetoxy groups at C-2, C-3, and C-4 were regioselectively deacetylated at C-4 position with Novozym 435. Antioxidant activities of free hydroxycinnamic acids and the respective β-d-xylopyranosides were evaluated by DPPH radical scavenging activity as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order ferulic acid>caffeic acid≈caffeoyl β-d-xylopyranosides≈sinapinic acid>sinapoyl β-d-xylopyranosides≈feruloyl β-d-xylopyranosides>p-coumaric acid>p-coumaroyl β-d-xylopyranosides. In bulk methyl linoleate, the antioxidant activity order against autoxidation was almost consistent with the scavenging activity order. The results showed that caffeoyl β-d-xylopyranosides and sinapoyl β-d-xylopyranosides were as effective as free caffeic acid, sinapinic acid, and ferulic acid.

Topics: Acetylation; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Enzymes, Immobilized; Free Radical Scavengers; Fungal Proteins; Glycosides; Glycosylation; Linoleic Acids; Lipase; Oxidation-Reduction; Picrates; Stereoisomerism; Xylose

In this study, ultrasound-assisted extraction (UAE) and other methods of extracting flavonoid compounds and ferulic acid (FA) from S. sinensis were investigated. Five different extraction methods, including water extraction (W), water extraction using UAE (W+U), 75% ethanol extraction (E), 75% ethanol extraction using UAE (E+U), and supercritical CO2 extraction (SFE) were applied in the extraction of bioactive compounds (flavonoids and ferulic acid) in order to compare their efficiency. The highest yield of flavonoids (4.28 mg/g) and ferulic acid (4.13 mg/g) content was detected in the E+U extract. Furthermore, S. sinensis extracts obtained by E+U show high antioxidant activity, and IC50 values of 0.47 mg/mL for DPPH radicals and 0.205 mg/mL for metal chelating activity. The total antioxidant assay shows superoxide radical scavenging capacity and in vitro mushroom tyrosinase inhibition in a dose-dependent manner, suggesting that E+U can be used for extraction of bioactive compounds from S. sinensis.

Topics: Biphenyl Compounds; Coumaric Acids; Ethanol; Flavonoids; Free Radical Scavengers; Fungal Proteins; Liquid-Liquid Extraction; Monophenol Monooxygenase; Orchidaceae; Picrates; Plant Extracts; Solvents; Sonication; Superoxides

Avenanthramides are characteristic constituents of oat seeds. We analyzed the methanol extract of oat seeds by HPLC and detected three compounds 1, 2, and 3 eluted at retention times similar to avenanthramides. The three compounds were purified by column chromatography and HPLC. Spectroscopic analyses of 1, 2, and 3 suggested that they are amides of 4,5-dihydroxyanthranilic acid with caffeic, p-coumaric, and ferulic acids, respectively. Their identities were confirmed by comparing spectra and chromatographic behavior with compounds synthesized from 4,5-dihydroxyanthranilic acid and N-hyrdroxysuccinimide esters of hydroxycinnamic acids. LC-MS/MS analysis with multiple reaction monitoring showed that the amounts of 1, 2, and 3 were 16.5-26.9% of corresponding avenanthamides with 5-hydroxyanthranilic acid. Compounds 1, 2, and 3 showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity than the corresponding avenanthramides with 5-hydroxyanthranilic acid, indicating the involvement of 4,5-dihydroxyanthranilic acid moiety in the scavenging of DPPH radicals.

Topics: Avena; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Free Radical Scavengers; Methanol; ortho-Aminobenzoates; Picrates; Plant Extracts; Propionates; Seeds; Solvents; Succinimides

Indocalamus latifolius (Keng) McClure leaf is a popular food material in East Asia due to its antioxidant and anticorrosive activities. To utilize it more effectively, we investigated the discrepancy of antioxidant activities and active compound content in Indocalamus latifolius leaf along with the altitude change. Total flavonoids, phenolics, titerpenoids and eight characteristic active constituents, i.e, orientin, isoorientin, vitexin, homovitexin, p-coumaric acid, chlorogenic acid, caffeic acid, and ferulic acid, were determined by UV-spectrophotometer and synchronous RP-HPLC, respectively. Antioxidant activity was measured using DPPH and FRAP methods. Our data showed that the content of TP and TF, DPPH radical scavenging ability and ferric reduction power of Indocalamus latifolius leaf changed as altitude altered, with the trends of decreasing gradually when lower than 700 m and then increasing to 1,000 m. Chlorogenic acid and orientin were the main characteristic compounds in Indocalamus latifolius leaf and were also affected by altitude. Our result indicated that higher altitude with an adverse environment is conducive to secondary metabolite accumulation for Indocalamus latifolius. It would provide a theoretical basis to regulate the leaf collection conditions in the industrial use of Indocalamus latifolius leaf.

Topics: Antioxidants; Apigenin; Asia; Biphenyl Compounds; Caffeic Acids; Chlorogenic Acid; Coumaric Acids; Diet; Ecosystem; Ferric Compounds; Flavonoids; Glucosides; Picrates; Plant Extracts; Plant Leaves; Poaceae; Polyphenols; Secondary Metabolism; Triterpenes

Terfezia boudieri Chatin (Scop.) Pers., is a famous macrofungus in the world as well as in Turkey for its pleasant aroma and flavour. People believe that this mushroom has some medicinal properties. Therefore, it is consumed as food and for medicinal purposes. Chloroform, acetone and methanol extracts of T. boudieri were tested to reveal its antimicrobial activity against four Gram-positive and five Gram-negative bacteria, and one yeast using a micro dilution method. In this study, the highest minimum inhibitory concentration (MIC) value was observed with the acetone extract (MIC, 4.8 µg/mL) against Candida albicans. Maximum antimicrobial effect was also determined with the acetone extract (MIC, 39-78 µg/mL). The scavenging effect of T. boudieri on 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radicals was measured as 0.031 mg/mL at 5 mg/mL concentration, and its reducing power was 0.214 mg/mL at 0.4 mg/mL. In addition, the phenolic contents were determined as follows: the catechin was 20 mg/g, the ferulic acid was 15 mg/g, the p-coumaric acid was 10 mg/g, and the cinnamic acid was 6 mg/g. The results showed that T. boudieri has antimicrobial activity on the gram negative and positive bacteria as well as yeast, and it also has a high antioxidant capacity. Therefore, T. boudieri can be recommended as an important natural food source.

Topics: Anti-Bacterial Agents; Antifungal Agents; Antioxidants; Bacteria; Biological Products; Biphenyl Compounds; Candida albicans; Catechin; Cinnamates; Coumaric Acids; Diet; Fungi; Humans; Phenols; Picrates

The antioxidant activities of ethanolic extract from edible mushroom Agaricus bisporus (A. bisporus) were evaluated by various methods in vitro and in vivo. In antioxidant assays in vitro, ethanolic extract of A. bisporus was found to have strong reducing power, superoxide radical, hydroxyl radical and 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, and moderate hydrogen peroxide scavenging activity. In antioxidant assays in vivo, mice were administered with ethanolic extract of A. bisporus via gavage for 30 consecutive days. As a result, administration of ethanolic extract significantly enhanced the activities of antioxidant enzymes in serums, livers and hearts of mice. In addition, the total phenolic content in the extract determined by Folin-Ciocalteu method was 6.18mg of gallic acid equivalents per gram of dry weight. The main phenolic compounds in ethanolic extract analyzed by ultra-high performance liquid chromatography tandem mass spectrometry were determined as gallic acid, protocatechuic acid, catechin, caffeic acid, ferulic acid and myricetin. These results suggested that ethanolic extract of A. bisporus had potent antioxidant activity and could be explored as a novel natural antioxidant.

Topics: Agaricus; Animals; Antioxidants; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Drug Evaluation, Preclinical; Enzymes; Ethanol; Female; Flavonoids; Free Radical Scavengers; Gallic Acid; Heart; Hydrogen Peroxide; Hydroxyl Radical; Liver; Mice; Picrates; Plant Extracts; Tandem Mass Spectrometry

Various glycosyl ferulates were efficiently synthesized from 2,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGB) with amine by amine-promoted glycosylation without using heavy metal. The resulted acetylated glycosyl ferulates with acetoxyl groups at C-2, C-3 and C-4 were regioselectively deacetylated at C-4 and C-6 positions with Novozym 435. Antioxidant abilities of free ferulic acids and its synthetic glycosyl ferulates were evaluated by inhibitory effect on autoxidation of bulk methyl linoleate as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH·) decreased in the order ferulic acid>sinapinic acid ≈ glycosyl sinapinates ≈ glycosyl ferulates>p-coumaric acid>glycosyl p-coumarates. In bulk methyl linoleate, the antioxidant activity order against autoxidation was very consistent with the scavenging activity order. The results showed that glycosyl ferulates and sinapinates were effective as well as free carboxylic acid forms.

Topics: Acetylation; Amines; Biocatalysis; Biphenyl Compounds; Candida; Chemistry Techniques, Synthetic; Coumaric Acids; Enzymes, Immobilized; Free Radical Scavengers; Fungal Proteins; Glycosylation; Hydrolysis; Linoleic Acids; Lipase; Oxidation-Reduction; Picrates; Stereoisomerism; Substrate Specificity

The purpose of this work was the synthesis, characterization and efficacy evaluation of new biocompatible antioxidant polymers linking trans-ferulic acid or a-lipoic acid. In particular, ferulic or lipoic acid were introduced in the preformed polymeric backbone. The new antioxidant biopolymers were characterized by Fourier transform infrared spectroscopy and gel permeation chromatography. The degree of functionalization (moles of antioxidant per gram of polymer) was determined by the Gaur-Gupta method for free amino group determination and by the Folin method for the phenolic groups. Their ability to inhibit lipid peroxidation were estimated in rat liver microsomal membranes induced in vitro by tert-BOOH (tert-butyl hydroperoxide), as a source of free radicals. The DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging effect was also evaluated. The obtained systems, with different solubility, showed strong antioxidant and antiradical activities, suggesting potential use as packaging materials for foods, cosmetics, pharmaceuticals and personal care products. Moreover, the cytotoxicity of the synthesized polymers was also evaluated on Caco-2 cell cultures in order to verify their biocompatibility when exposed to an absorptive epithelial cell line.

Topics: Acrylamides; Acrylic Resins; Animals; Biocompatible Materials; Biphenyl Compounds; Caco-2 Cells; Cell Survival; Coumaric Acids; Free Radical Scavengers; Free Radicals; Humans; Inhibitory Concentration 50; Lipid Peroxidation; Malondialdehyde; Methacrylates; Microsomes, Liver; Picrates; Rats; Rats, Wistar; Spectroscopy, Fourier Transform Infrared; Thioctic Acid

Rhizoma Atractylodes macrocephala (AM) has been used in Traditional Chinese Medicine (TCM) for about 2,000 years. In the study, we firstly determined the antioxidant levels of five AM extracts by •OH-scavenging, •O2−-scavenging, Fe2+-chelating, Cu2+-chelating, DPPH·-scavenging, and ABTS+·-scavenging assays. After measurement of the chemical contents in five AM extracts, we quantitatively analyzed the correlations between antioxidant levels and chemical contents. It was observed that total phenolics and total flavonoids had significant positive correlations with antioxidant levels (R = 0.685 and 0.479, respectively). In contrast, total sugars and total saponins presented lower correlations with antioxidant levels (R=−0.272 and 0.244, respectively). It means that antioxidant activity of AM should be attributed to total phenolics (including phenolic acids and flavonoids), and not total sugars and total saponins. Further analysis indicated that phenolic acids exhibited higher R values with radical-scavenging assays (R=0.32–1.00), while flavonoids showed higher R values with metal-chelating assays (R=0.86 and 0.90). In conclusion, AM exerts its antioxidant effect through metal-chelating, and radical-scavenging which is via donating hydrogen atom and donating electron. Its metal-chelating may result from flavonoids, while its radical-scavenging can be attributed to phenolic acids, especially caffeic acid, ferulic acid, and protocatechuic acid.

Topics: Atractylodes; Benzothiazoles; Biphenyl Compounds; Caffeic Acids; Copper; Coumaric Acids; Drugs, Chinese Herbal; Flavonoids; Free Radical Scavengers; Hydroxybenzoates; Hydroxyl Radical; Iron; Liquid-Liquid Extraction; Oxidants; Picrates; Rhizome; Sulfonic Acids; Superoxides

Ferulic acid (FA), an organic UV absorber and free radical scavenger, was intercalated into an inorganic zinc basic salt (ZBS) matrix to prepare a UV screening material. FA molecules were vertically oriented bilayer in the ZBS lattice with an expansion of approximately 22.7 angstroms along the c-axis. The FA-ZBS nanohybrid exhibited a superior UV-A approximately UV-B screening ability and an antioxidant activity that was comparable to that of a pure FA molecule. The in vitro release test showed the biphasic release of the FA molecules from the FA-ZBS nanohybrid that consisted of an initial burst, followed by a slow and sustained release.

Topics: Biphenyl Compounds; Coumaric Acids; Delayed-Action Preparations; Drug Stability; Nanocomposites; Picrates; Powder Diffraction; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Sunscreening Agents; Ultraviolet Rays; Zinc

Aromatic ester derivatives of ferulic acid where the phenolic hydroxyl is free (6a-d) or acetylated (5a-d) were evaluated for their antioxidant and antimicrobial properties. The superoxide radical scavenging capacity of compounds 5d and 6d-e (IC(50) of 0.19, 0.27 and 0.20 mM, respectively) was found to be twice as active as α-tocopherol (IC(50) = 0.51 mM). DPPH radical scavenging capacity was moderate and only found in compounds bearing free phenolic hydroxyl groups (6a-e). With regard to antimicrobial properties, compounds 6b and 6c displayed significant activity against Enterococcus faecalis (MICs = 16 μg/mL) and vancomycin-resistant E. faecalis (MIC for 6b, 32 and for 6c, 16 μg/mL). Compound 6c also demonstrated prominent activity against planktonic Staphylococcus aureus with a MIC value of <8 μg/mL and it inhibited bacterial biofilm formation by S. aureus with a MBEC value of <8 μg/mL, which was 64 and 128 times more potent than ofloxacin and vancomycin, respectively.

Topics: Anti-Bacterial Agents; Antioxidants; Biofilms; Biphenyl Compounds; Candida albicans; Coumaric Acids; Enterococcus faecalis; Escherichia coli; Esters; Free Radical Scavengers; Klebsiella pneumoniae; Lipid Peroxidation; Microbial Sensitivity Tests; Picrates; Staphylococcus aureus; Superoxides

The present study evaluated the radical scavenging and angiotensin converting enzyme (ACE) inhibitory activity of cold and hot aqueous extracts of Ficus racemosa (Moraceae) stem bark. The extracts were standardized using HPLC. Radical scavenging activity was determined using 1,1-diphenyl-2-picrylhydrazyl radical and angiotensin converting enzyme inhibitory activity using rabbit lung and partially purified porcine kidney ACE. HPLC profiles of cold aqueous extract (FRC) showed the presence of bergenin, an isocoumarin, while hot aqueous extract (FRH) was found to contain ferulic acid, kaempferol and coumarin in addition to bergenin. FRH showed significantly higher (p ≤ 0.01) radical scavenging activity than FRC and butylated hydroxytoluene (BHT), consequently resulting in a significantly lower (p ≤ 0.01) IC₅₀ value than FRC and BHT. Both the extracts exhibited a dose dependent inhibition of porcine kidney and rabbit lung ACE. FRH showed significantly higher (p ≤ 0.01) activity than FRC with lower IC(50) values of 1.36 and 1.91 μg/mL respectively, for porcine kidney and rabbit lung ACE, compared with those of FRC (128 and 291 μg/mL). Further, a significant correlation (r = 0.893; p ≤ 0.05) was observed between radical scavenging activity and ACE-inhibitory activity. This is the first report on the ACE-inhibitory activity of F. racemosa stem bark suggesting its potential to be utilized as a therapeutic alternative for hypertension.

Topics: Angiotensin-Converting Enzyme Inhibitors; Animals; Benzopyrans; Biphenyl Compounds; Coumaric Acids; Coumarins; Ficus; Free Radical Scavengers; Kaempferols; Lung; Picrates; Plant Bark; Plant Extracts; Rabbits; Swine

Dietary polyphenols are beneficial to human health by exerting various biological effects. Ferulic and caffeic acids are hydroxycinnamic acid derivatives widely distributed in plant-derived food products. Studies indicate that some dietary compounds may have concentration-dependent antioxidant or prooxidant activities. The present study concerns such activities of ferulic and caffeic acids. They have concentration-dependent antioxidant effects in terms of inhibition of lipid peroxidation and reactive oxygen species-scavenging after 2,2'-azobis-amidinopropane dihydrochloride-induced damage in mouse liver microsomes and splenic lymphocytes respectively. They also show differential scavenging of nitric oxide, superoxide and 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid radical (ABTS*(+)). In DPPH (1,1-diphenyl picrylhydrazyl) assay above 20 μM the absorbance start increasing due to the formation of an unknown adduct which has a shoulder at 517 nm. However, in Fenton reaction, above 5 μM, they behave as prooxidants and the possible mechanisms responsible for their prooxidant property may be related to their ferric reducing ability. These findings may have significant health implications where these natural compounds are being used/consumed.

Topics: Amidines; Animals; Antioxidants; Benzothiazoles; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Ferric Compounds; Free Radical Scavengers; Hydroxyl Radical; In Vitro Techniques; Lipid Peroxidation; Male; Mice; Microsomes, Liver; Nitric Oxide; Oxidants; Picrates; Reducing Agents; Sulfonic Acids; Superoxides

This study investigated the effects of processing conditions including bran particle size, dough fermentation time, and baking time and temperature on the extractable antioxidant properties of whole-wheat pizza crust. Experiments were carried out using two different varieties of hard white winter wheat, Trego and Lakin. Antioxidant properties examined included oxygen radical absorbing capacity (ORAC), hydroxyl radical scavenging capacity (HOSC), relative 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity (RDSC), cation 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) radical scavenging capacity, total phenolic contents (TPC), and ferulic acid contents. Results indicated that bran particle size had no effect on the antioxidant properties evaluated. Increasing dough fermentation time from 0 to 48 h had no significant influence on antioxidant properties except HOSC, which increased as much as 28%, possibly as a result of increase in soluble free ferulic acid, which increased as much as 130%. Increasing baking temperature from 204 to 288 degrees C with a 7 min bake time increased all evaluated antioxidant properties by as much as 82%. Increasing baking time from 7 to 14 min with 204 degrees C baking temperature might increase some antioxidant properties as much as 60%. The results from this study suggest that longer dough fermentation times and increased baking time or temperature may be potential approaches to increase the antioxidant availability in whole-wheat pizza crust.

Topics: Antioxidants; Biphenyl Compounds; Bread; Coumaric Acids; Dietary Fiber; Fermentation; Hot Temperature; Hydroxyl Radical; Particle Size; Picrates; Reactive Oxygen Species; Triticum

1,3-Diferuloyl-sn-glycerol is found ubiquitously throughout the plant kingdom, possessing ultraviolet adsorbing and antioxidant properties. Diferuloyl glycerol was synthesized and isolated as a byproduct in up to 5% yield from a pilot plant scale packed-bed, biocatalytic transesterification of ethyl ferulate with soybean oil or mono- and diacylglycerols from soybean oil. The yield of the diferuloyl glycerol byproduct was directly proportional to the overall water concentration of the bioreactor. The isolated diferuloyl glycerol exhibited good ultraviolet adsorbing properties, 280-360 nm with a lambda(max) 322 nm, and compared well to the efficacy of commercial sunscreen active ingredients. The antioxidant capacity of diferuloyl glycerol (0.25-2.5 mM) was determined by its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl radicals and was comparable to that of ferulic acid. At current pilot plant scale production capacity, 120 kg diferuloyl glycerol byproduct could be isolated per year.

Topics: Antioxidants; Bioreactors; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Glycerol; Glycine max; Picrates; Soybean Oil; Spectrum Analysis; Sunscreening Agents; Ultraviolet Rays

The first glycosylated isoferulic acid, isoferulic acid 3-O-beta-glucopyranoside, together with the new phenolics, tamarixetin 3,3'-di-sodium sulphate and dehydrodigallic acid dimetyl ester have been characterized from a flower extract of Tamarix aphylla. The structures were established on the basis of spectral data. The extract exhibited a distinct radical scavenging effect and to improve the viability of human keratinocytes (HaCaT cells). Also, the known isoferulic acid and ferulic acid which have been determined to be the major components of the investigated extract by HPLC/ESI mass spectrometric screening have been separated, characterized and evaluated as active antioxidants and as cell activity stimulating agents as well.

Topics: Antioxidants; Biphenyl Compounds; Cell Differentiation; Cell Line; Cell Survival; Chromatography, High Pressure Liquid; Cinnamates; Coloring Agents; Coumaric Acids; Flowers; Free Radical Scavengers; Glucosides; Humans; Keratinocytes; Methanol; Phenols; Picrates; Plant Extracts; Solvents; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Ultraviolet; Tamaricaceae; Tetrazolium Salts; Thiazoles

Lipase-catalyzed transesterification of flaxseed oil with cinnamic acid (CA) or ferulic acid (FA) using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. Lipase-catalyzed transesterification of flaxseed oil with CA or FA produced a variety of lipophilized products (identified using ESI-MS-MS) such as monocinnamoyl/feruloyl-diacylglycerol, dicinnamoyl-monoacylglycerol and monocinnamoyl-monoacylglycerol. The free radical scavenging activity of the lipophilized products of lipase-catalyzed transesterification of flaxseed oil with CA or FA toward 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) were both examined in ethanol and ethyl acetate. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Unesterified FA showed the highest free radical scavenging activity among all substrates tested while CA had negligible activity. The esterification of CA or FA with flaxseed oil resulted in significant increase and decrease in the radical scavenging activity compared with the native phenolic acid, respectively. Based on the ratio of a substrate to DPPH. concentration, lipophilized FA was a much more efficient free radical scavenger compared to lipophilized CA and was able to provide enhanced antioxidant activity in the flaxseed oil. Lipophilized cinnamic acid did not provide enhanced radical scavenging activity in the flaxseed oil as the presence of natural hydrophilic antioxidants in the oil had much greater radical scavenging activity.

Topics: Biphenyl Compounds; Candida; Chromatography, High Pressure Liquid; Cinnamates; Coumaric Acids; Enzymes, Immobilized; Esterification; Free Radical Scavengers; Linseed Oil; Lipase; Picrates; Spectrometry, Mass, Electrospray Ionization

Polyphenols have been shown to induce apoptosis in a variety of tumor cells including leukemia both in vitro and in vivo. However, their action on normal human peripheral blood mononuclear cells (PBMCs) during oxidative stress remains to be explored. In this study, we have evaluated the anti-apoptotic and radical scavenging activities of dietary phenolics, namely caffeic acid (CA), ellagic acid (EA) and ferulic acid (FA). H2O2-induced apoptosis in normal human PBMCs was assayed by phosphotidylserine externalization, nucleosomal damage and DNA fragmentation. Incubation of PBMCs with 5 mM H2O2 led to increased Annexin-V binding to externalized phosphatidyl serine (PS), an event of pre-apoptotic stage of the cell. Peripheral blood mononuclear cells pretreated with phenolics could resist H2O2-induced apoptotic damage. Caffeic acid (60 and 120 microM) and EA (100 and 200 microM) caused no change in externalization of PS, whereas FA (100 and 200 microM) increased externalization of PS in PBMCs treated with H2O2. The effects of phenolics were abolished to a large extent by culturing the PBMCs for 24 h after washing the phenolics from the medium. Inhibitory activities of these phenolics on lipid peroxidation were in the order of EA

Topics: Antioxidants; Apoptosis; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Ellagic Acid; Flavonoids; Humans; Hydrogen Peroxide; Leukocytes, Mononuclear; Lipid Peroxidation; Oxidative Stress; Phenols; Picrates; Polyphenols; Proto-Oncogene Proteins c-bcl-2

A strong radical-scavenging activity against a stable radical compound, 1,1-diphenyl-2-picrylhydrazyl (DPPH) was found in the hot water extract of Japanese rice bran. When the extract was treated with ethanol, a dominant radical-scavenging activity was observed in the ethanol-soluble (ES) fraction in a dose-dependent manner, but a weak radical-scavenging activity was detected in the ethanol-precipitable (EP) fraction. Their activities were proportional to the amounts of phenolic substances in each fraction. The phenolic substances in the ES fraction were efficiently separated by Amberlite XAD column chromatography and high performance liquid chromatography using an ODS column. The four major phenolic acids (ferulic, para-coumaric, para-hydroxybenzoic and vanillic acids) and four minor phenolic acids (caffeic, gentisic, protocatechuic and syringic acids) were detected in the HPLC system. Among these phenolic acids, protocatechuic, caffeic, ferulic and gentisic acids showed relatively strong radical scavenging activities (EC50: 8, 9, 29 and 75 microM, respectively) compared with the control antioxidants such as ascorbic acid and alpha-tocopherol (EC50: 93 and 134 microM). Para-coumaric, syringic and vanillic acids exhibited weak but significant radical-scavenging activities (EC50: 780, 2640 and 3250 microM). However, para-hydroxybenzoic acid did not show any significant effects even at 5 mM. Furthermore, a simulated mixture combined with these phenolic acids in comparable amounts in the ES fraction showed slightly weak radical-scavenging activity compared with that of rice bran extract. However, all the phenolic acids detected in the ES fraction did not show significant antioxidant activities against hydroperoxide generation in lipid peroxidation compared with that of a typical antioxidant such as ascorbic acid, which was estimated by the alminum chloride method. These results suggest that Japanese rice bran has a potent radical-scavenging activity against DPPH radical and this activity is associated with some phenolic acids in the ES fraction. The significance of this finding is discussed from the viewpoint of the protective role of rice bran against oxygen radical-induced chronic diseases.

Topics: Biphenyl Compounds; Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Dose-Response Relationship, Drug; Ethanol; Free Radical Scavengers; Gentisates; Hot Temperature; Hydrazines; Hydroxybenzoates; Oryza; Picrates; Plant Extracts; Solubility; Water

Commercially available enzyme preparations were screened for enzymes that have a high ability to catalyze direct ester-synthesis of ferulic acid with glycerol. Only a preparation, Pectinase PL "Amano" produced by Aspergillus niger, feruloylated glycerol under the experimental conditions. The enzyme responsible for the esterification was purified and characterized. This enzyme, called FAE-PL, was found to be quite similar to an A. niger ferulic acid esterase (FAE-III) in terms of molecular mass, pH and temperature optima, substrate specificity on synthetic substrates, and the N-terminal amino acid sequence. FAE-PL highly catalyzed direct esterification of ferulic acid and sinapinic acid with glycerol. FAE-PL could feruloylate monomeric sugars including arabinose, fructose, galactose, glucose, and xylose. We determined the suitable conditions for direct esterification of ferulic acid with glycerol to be as follows: 1% ferulic acid in the presence of 85% glycerol and 5% dimethyl sulfoxide at pH 4.0 and 50 degrees C. Under these conditions, 81% of ferulic acid could be converted to 1-glyceryl ferulate, which was identified by (1)H-NMR. The ability of 1-glyceryl ferulate to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals was higher than that of the anti-oxidant butyl hydroxytoluene.

Topics: Antioxidants; Aspergillus niger; Biphenyl Compounds; Catalysis; Coumaric Acids; Esterases; Free Radicals; Glycerol; Hydrazines; Hydrogen-Ion Concentration; Hydrolysis; Magnetic Resonance Spectroscopy; Models, Chemical; Monoglycerides; Picrates; Polymers; Protein Structure, Tertiary; Substrate Specificity; Temperature

The scavenging behavior of a series of catechol and guaiacol acid derivatives toward DPPH(*) was examined having as a starting point the order of activity derived on the basis of theoretically calculated BDE values. The studied compounds were protocatechuic, homoprotocatechuic, dihydrocaffeic, and caffeic acids and also vanillic, homovanillic, dihydroferulic, and ferulic acids. Catechol and guaiacol were used as reference compounds. Observations from the parallel study were made with regard to structural features (number and position of hydroxyl groups and the side-carbon chain characteristics) that regulated the behavior of the compounds experimentally. The exceptional DPPH(*) scavenging behavior observed for homoprotocatechuic acid in ethanol and for caffeic acid in acetonitrile could not be supported by the respective BDE values. Ferulic was the most active among guaiacolic acids, whereas dihydroferulic exhibited the highest stoichiometry. Ionizable carboxylic groups seem to affect considerably the relative order of activity as was also evidenced using the ORAC assay. Questions raised about the validity of widely accepted views on criteria for SARs are discussed with regard to literature findings.

Topics: 3,4-Dihydroxyphenylacetic Acid; Biphenyl Compounds; Caffeic Acids; Catechols; Coumaric Acids; Free Radical Scavengers; Guaiacol; Picrates; Structure-Activity Relationship; Thermodynamics

Eugenol, isoeugenol, caffeic acid, ferulic acid, isoferulic acid, estragole, trans-anethole, and paeonol are components of a Chinese herbal medicine used as a painkiller and stomachic. We investigated the potential role of these compounds as antioxidants. We studied the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging effect of these molecules, together with some glycoside derivatives, to ascertain their potential in reducing the levels of activated oxygen species in vivo. The DPPH radical-scavenging effects of eugenol, isoeugenol, and the glycoside derivatives of caffeic acid, ferulic acid, and isoferulic acid (SC(50)=8-28 microM) were similar to those of alpha-tocopherol, which was used as a positive control.

Topics: Antioxidants; Biphenyl Compounds; Caffeic Acids; Cinnamates; Coumaric Acids; Eugenol; Free Radical Scavengers; Glycosides; Picrates; Reactive Oxygen Species; Structure-Activity Relationship

An electron spin resonance (ESR) spectrometry study was conducted to examine the free radical scavenging properties of bran extracts of Alliance and Wichita wheat using hydroxyl radical (HO*), 2,2-diphenyl-1-picryhydrazyl radical (DPPH*), and superoxide radical anion (O2*-) and their chelating capacities against Cu2+. Also reported is the radical cation 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS*+) scavenging activity, oxygen radical absorbing capacity (ORAC), and chelating property against Fe2+ of the bran extracts measured by the spectrophotometric methods. Significant radical scavenging and chelating capacities were detected in the bran extracts, along with significant levels of phenolic acids, tocopherols, and carotenoids. Ferulic acid, with a concentration range of 130.60-146.38 microg/g, was the predominant phenolic acid in all of the tested bran samples and accounted for approximately 53-67% of total phenolic acids on a weight basis. Total tocopherol concentration ranged from 1.87 to 2.95 micromol/100 g of bran, whereas total carotenoid level was 0.20-0.33 micromol/100 g of bran. In addition, both wheat variety and growing conditions might significantly alter antioxidant properties and concentrations of beneficial components in wheat bran.

Topics: Antioxidants; Biphenyl Compounds; Carotenoids; Copper; Coumaric Acids; Dietary Fiber; Electron Spin Resonance Spectroscopy; Ferrous Compounds; Hydroxybenzoates; Hydroxyl Radical; Picrates; Superoxides; Tocopherols

The kinetic behavior of cinnamic acids, their methyl esters, and two catechols 1-10 (ArOH) in the reaction with DPPH(*) in methanol and ethanol is not compatible with a reaction mechanism that involves hydrogen atom abstraction from the hydroxyl group of 1-10 by DPPH(*). The rate of this reaction at 25 degrees C is, in fact, comparatively fast despite that the phenolic OH group of ArOH is hydrogen bonded to solvent molecules. The observed rate constants (k(1)) relative to DPPH(*) + ArOH are 3-5 times larger for the methyl esters than for the corresponding free acids and, for the latter, decrease as their concentration is increased according to the relation k(1) = B/[ArOH](0)(m), where k(1) is given in units of M(-1) s(-1), m is ca. 0.5, and B ranges from 0.02 (p-coumaric acid) to ca. 3.48 (caffeic acid) in methanol and from 0.04 (p-coumaric acid) to ca. 13 (sinapic acid) in ethanol. Apparently, the reaction mechanism of DPPH(*) + ArOH involves a fast electron-transfer process from the phenoxide anion of 1-10 to DPPH(*). Kinetic analysis of the reaction sequence for the free acids leads to an expression for the observed rate constant, k(1), proportional to [ArOH](0)(-1/2) in excellent agreement with the experimental behavior of these phenols. The experimental results are also interpreted in terms of the influence that adventitious acids or bases present in the solvent may have. These impurities dramatically influence the ionization equilibrium of phenols and cause a reduction or an enhancement, respectively, of the measured rate constants.

Topics: Alcohols; Biphenyl Compounds; Caffeic Acids; Cinnamates; Coumaric Acids; Electrochemistry; Electron Transport; Esters; Kinetics; Methane; Models, Chemical; Molecular Structure; Oxidation-Reduction; Picrates; Solutions

The antioxidant activity of some esters of ferulic acid with the linear fatty alcohols C7, C8 (branched and linear), C9, C11, C12, C13, C15, C16, and C18 has been studied in homogeneous and heterogeneous phases. Whereas in homogeneous phase all of the alkyl ferulates possessed similar radical-scavenging abilities, in rat liver microsomes they showed striking differences, the more effective being C12 (7) (IC50 = 11.03 M), linear C8 (3) (IC50 = 12.40 microM), C13 (8) (IC50 = 18.60 microM), and C9 (5) (IC50 = 19.74 microM), followed by C7 (2), C15 (9), C11 (6), branched C8 (4), C16 (10), and C18 (11) (ferulic acid was the less active, IC50 = 243.84 microM). All of the molecules showed similar partition coefficients in an octanol-buffer system. Three-dimensional studies (NMR in solution, modeling in vacuo) indicate that this behavior might be due to a different anchorage of the molecules with the ester side chain to the microsomal phospholipid bilayer and to a consequent different orientation/positioning of the scavenging phenoxy group outside the membrane surface against the flux of oxy radicals.

Topics: Alkylation; Animals; Antioxidants; Biphenyl Compounds; Coumaric Acids; Esters; Fatty Alcohols; Magnetic Resonance Spectroscopy; Male; Microsomes, Liver; Peroxides; Picrates; Rats; Rats, Wistar

Higher alcohols with a carbon length ranging from 16 to 30 found in the lipophilic fraction from potato pulp were shown to be present as ferulate and in a free form, but not as wax. Thin-layer chromatography of the neutral lipids in potato pulp indicated a few spots with scavenging activity toward the 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable radical, the major active component being characterized as alkyl ferulate which showed almost the same level of activity as gamma-oryzanol.

Topics: Alcohols; Biphenyl Compounds; Chromatography, Thin Layer; Coumaric Acids; Free Radical Scavengers; Gas Chromatography-Mass Spectrometry; Hydrazines; Lipids; Picrates; Solanum tuberosum

Differences in the antioxidant activity of some biosynthetically related ferulic acid derivatives induced by the presence of characteristic groups (-COOH, -CHO, -CH(2)OH, -CH(3), and -COOC(2)H(5)) at the end of their carbon side chain were investigated using both experimental and computational methods. The relative order of the scavenging activity toward the DPPH radical derived from kinetic studies was isoeugenol approximately coniferyl alcohol >> ferulic acid approximately coniferyl aldehyde approximately ethyl ferulate. In bulk oil autoxidation (45 degrees C) the same order of activity was obtained. In the o/w emulsion autoxidation, lipophilicity of the phenols was the determining factor because the least polar compounds bearing -CH(3) and -COOC(2)H(5) were the most effective ones. The order of activity based on the O-H bond dissociation enthalpy (BDE) and ionization potential (IP) values, calculated by the density functional theory (DFT) method, was in accordance with the experimental radical scavenging order and with the electron-donating/withdrawing properties of the characteristic groups. Other molecular descriptors could not complement the experimental findings.

Topics: Antioxidants; Biphenyl Compounds; Chemical Phenomena; Chemistry, Physical; Coumaric Acids; Free Radical Scavengers; Lipid Peroxidation; Picrates; Structure-Activity Relationship; Thermodynamics

The extract of garlic skins (peels) showed strong antioxidant activity, and some responsible constituents were isolated and identified. Garlic (Allium sativum L.) has been used as an herbal medicine, but there is no report on the health benefits of the skin or peel. In this study, the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity of garlic skin extract was evaluated. Using chromatographic techniques, the active constituents were isolated and subsequently identified. Analyses by high-performance liquid chromatography coupled with a photodiode array detector (HPLC-PDA) suggested that these compounds were phenylpropanoids, which had a characteristic absorbance at 300-320 nm. Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance analyses allowed the chemical structures of the isolated constituents to be postulated. The proposed compounds were subsequently synthesized and compared with the constituents in the extract using HPLC-PDA and LC-MS. N-trans-Coumaroyloctopamine, N-trans-feruloyloctopamine, guaiacylglycerol-beta-ferulic acid ether, and guaiacylglycerol-beta-caffeic acid ether were identified as were trans-coumaric acid and trans-ferulic acid. Also, the antioxidant activities of these compounds were determined.

Topics: Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Cinnamates; Coumaric Acids; Ethanol; Garlic; Magnetic Resonance Spectroscopy; Mass Spectrometry; Picrates; Plant Extracts; Plant Structures

Dihydroferulic acid (DFA) and dihydrosinapic acid (DSA) were isolated from Kurosu (unpolished rice vinegar) as the major constituents responsible for Kurosu's radical scavenging activity. The levels of antioxidative activity of DFA and DSA in DPPH radical scavenging were higher than those of their respective structurally related compounds, ferulic acid and sinapic acid. The concentrations of DFA and DSA were low in common rice vinegar (polished rice vinegar), suggesting that Kurosu is more advantageous than rice vinegars as an antioxidative food item. As the concentrations of DFA and DSA were low in unpolished rice, too, these acids are thought to be produced in Kurosu through the process of the fermentation from ferulic acid and sinapic acid, respectively.

Topics: Acetic Acid; Antioxidants; Biphenyl Compounds; Coumaric Acids; Fermentation; Free Radical Scavengers; Free Radicals; Japan; Oryza; Picrates

Antioxidant activity of 24 ferulic acid related compounds together with 6 gallic acid related compounds was evaluated using several different physical systems as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order caffeic acid > sinapic acid > ferulic acid > ferulic acid esters > p-coumaric acid. In bulk methyl linoleate, test hydroxycinnamic acids and ferulic acid esters showed antioxidant activity in parallel with their radical scavenging activity. In an ethanol-buffer solution of linoleic acid, the activity of test compounds was not always associated with their radical scavenging activity. Ferulic acid was most effective among the tested phenolic acids. Esterification of ferulic acid resulted in increasing activity. The activity of alkyl ferulates was somewhat influenced by the chain length of alcohol moiety. When the inhibitory effects of alkyl ferulates against oxidation of liposome induced by AAPH were tested, hexyl, octyl, and 2-ethyl-1-hexyl ferulates were more active than the other alkyl ferulates. Furthermore, lauryl gallate is most effective among the tested alkyl gallates. These results indicated that not only the radical scavenging activity of antioxidants, but also their affinity with lipid substrates, might be important factors in their activity.

Topics: Antioxidants; Bepridil; Biphenyl Compounds; Buffers; Caffeic Acids; Coumaric Acids; Esterification; Ethanol; Free Radical Scavengers; Free Radicals; Gallic Acid; Hot Temperature; Linoleic Acid; Liposomes; Oryza; Picrates; Plant Structures; Solutions

Seven antioxidative serotonin derivatives were isolated from safflower (Carthamus tinctorius L.) oil cake. Their structures were established as N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]ferulamide (1), N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-p-coumaramide (2), N,N'-[2,2'-(5,5'-dihydroxy-4,4'-bi-1H-indol-3,3'-yl)diethyl]- di-p-coumaramide (3), N-[2-[3'-[2-(p-coumaramido)ethyl]-5,5'-dihydroxy- 4,4'-bi-1H-indol-3-yl]ethyl]ferulamide (4), and N,N'-[2,2'-(5,5'-dihydroxy-4,4'-bi-1H-indol-3,3'-yl)diethyl]- diferulamide (5), N-[2-[5-(beta-D-glucosyloxy)-1H-indol-3-yl)ethyl]- p-coumaramide (6), and N-[2-[5-(beta-D-glucosyloxy)-1H-indol-3-yl)ethyl]ferulamide (7). Antioxidative activities of the compounds were measured by the ferric thiocyanate method and the alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) method, and compounds 1-5 were found to have relatively strong antioxidative activity.

Topics: Antioxidants; Bepridil; Biphenyl Compounds; Coumaric Acids; Free Radical Scavengers; Indicators and Reagents; Iron; Magnetic Resonance Spectroscopy; Picrates; Propionates; Safflower Oil; Serotonin; Spectrometry, Mass, Fast Atom Bombardment; Thiocyanates

Topics: Animals; Bepridil; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Free Radicals; Glucosides; In Vitro Techniques; Lipid Peroxidation; Liver; Male; Mitochondria, Liver; Oxygen Consumption; Phenols; Picrates; Plant Extracts; Rats; Rats, Wistar; Reperfusion Injury; Vitamin E