1-1-diphenyl-2-picrylhydrazyl and sinapinic-acid

For investigation of antioxidant capacity relationship, four cinnamic acids (CNAs), including cinnamic (CA), ferulic (FA), p-coumaric (p-CA) and sinapic (SA) acids, were selected to modify porous starch (PS) with different degrees of substitution by esterification, respectively. The ester linkage of CNAs modified PS was confirmed by

Topics: Antioxidants; Biphenyl Compounds; Carbon Isotopes; Cinnamates; Coumaric Acids; Crystallization; Electrons; Esters; Food Industry; Food Technology; Free Radical Scavengers; Free Radicals; Hydrogen; Hydroxyl Radical; Magnetic Resonance Spectroscopy; Microscopy, Electron, Scanning; Phenol; Picrates; Porosity; Solanum tuberosum; Solubility; Spectroscopy, Fourier Transform Infrared; Starch

Modified mustard varieties can produce edible oil with reduced amounts of erucic acid and glucosinolates and enhanced antioxidant potential. Therefore, this work focused on the optimisation of the ultrasound-assisted extraction of compounds with high antioxidant capacity from three white mustard seed cultivars using response surface methodology.. The predicted optimum solvent polarity (57.2, 56.5 and 57.6) and ultrasound power-to-sonication time ratio (4.5, 4.8 and 4.3 W min(-1)) resulted in antioxidant capacities determined by the ferric-reducing antioxidant power (FRAP) assay [54.37, 65.75 and 68.55 mmol Trolox equivalent (TE) kg(-1)] and the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) method (141.65, 175.26 and 185.10 mmol TE kg(-1)) and total phenolics content (23.70, 27.16 and 11.29 mg sinapic acid g(-1)) for extracts obtained from one traditional and two modified mustard seed varieties. The highest FRAP and DPPH values (69.51 and 197.73 mmol TE kg(-1)) revealed 50% methanolic extract prepared from modified mustard seed cultivar without erucic acid and glucosinolates treated with ultrasound for 30 min (ultrasound power/ultrasound time = 4 W min(-1)).. Ultrasound-assisted extraction was found to be a more rapid, convenient and appropriate extraction method with higher yield of antioxidants, shorter time and lower solvent consumption in comparison to conventional extraction.

Topics: Antioxidants; Biphenyl Compounds; Coumaric Acids; Mustard Plant; Phenols; Picrates; Plant Extracts; Seeds; Sonication; Species Specificity; Spices; Ultrasonics

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

Sinapic acid is a member of the phenylpropanoid family and is abundant in cereals, nuts, oil seeds, and berries. It exhibits a wide range of pharmacological properties. In this study, we investigated the hepatoprotective and antifibrotic effects of sinapic acid on dimethylnitrosamine (DMN)-induced chronic liver injury in rats. Sinapic acid remarkably prevented DMN-induced loss of body weight. This was accompanied by a significant increase in levels of serum alanine transaminase, aspartate transaminase, and liver malondialdehyde content. Furthermore, sinapic acid reduced hepatic hydroxyproline content, which correlated with a reduction in the expression of type I collagen mRNA and histological analysis of collagen in liver tissue. Additionally, the expression of hepatic fibrosis-related factors such as α-smooth muscle actin and transforming growth factor-β1 (TGF-β1), were reduced in rats treated with sinapic acid. Sinapic acid exhibited strong scavenging activity. In conclusion, we find that sinapic acid exhibits hepatoprotective and antifibrotic effects against DMN-induced liver injury, most likely due to its antioxidant activities of scavenging radicals, its capacity to suppress TGF-β1 and its ability to attenuate activation of hepatic stellate cells. This suggests that sinapic acid is a potentially useful agent for the protection against liver fibrosis and cirrhosis.

Topics: Animals; Biphenyl Compounds; Blotting, Western; Coumaric Acids; Dimethylnitrosamine; Free Radical Scavengers; Lipid Peroxidation; Liver Cirrhosis, Experimental; Liver Function Tests; Male; Molecular Structure; Picrates; Rats; Rats, Sprague-Dawley; Reverse Transcriptase Polymerase Chain Reaction; Transcription Factor RelA; Transforming Growth Factor beta1

Inhibition of oxidative stress and inflammation in vascular endothelial cells (ECs) may represent a new therapeutic strategy against endothelial activation. Sinapic acid (SA), a phenylpropanoid compound, is found in natural herbs and high-bran cereals and has moderate antioxidant activity. We aimed to develop new SA agents with the properties of antioxidation and blocking EC activation for possible therapy of cardiovascular disease. We designed and synthesized 10 SA derivatives according to their chemical structures. Preliminary screening of the compounds involved scavenging hydroxyl radicals and 2,2-diphenyl-1-picrylhydrazyl (DPPH(⋅)), croton oil-induced ear edema in mice, and analysis of the mRNA expression of adhesion molecules in ECs. 1-Acetyl-sinapic acyl-4-(3'-chlorine-)benzylpiperazine (SA9) had the strongest antioxidant and anti-inflammatory activities both in vitro and in vivo. Thus, the effect of SA9 was further studied. SA9 inhibited tumor necrosis factor α-induced upregulation of adhesion molecules in ECs at both mRNA and protein levels, as well as the consequent monocyte adhesion to ECs. In vivo, result of face-to-face immunostaining showed that SA9 reduced lipopolysaccharide-induced expression of intercellular adhesion molecule-1 in mouse aortic intima. To study the molecular mechanism, results from luciferase assay, nuclear translocation of NF-κB, and Western blot indicated that the mechanism of the anti-inflammatory effects of SA9 might be suppression of intracellular generation of ROS and inhibition of NF-κB activation in ECs. SA9 is a prototype of a novel class of antioxidant with anti-inflammatory effects in ECs. It may represent a new therapeutic approach for preventing endothelial activation in cardiovascular disorders.

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Aorta; Biphenyl Compounds; Cell Adhesion; Coumaric Acids; Croton Oil; Ear; Edema; Endothelial Cells; Endothelium, Vascular; Free Radical Scavengers; Human Umbilical Vein Endothelial Cells; Humans; Inflammation; Intercellular Adhesion Molecule-1; Lipopolysaccharides; Mice; Mice, Inbred BALB C; Mice, Inbred C57BL; Monocytes; NF-kappa B; Oxidative Stress; Picrates; Tumor Necrosis Factor-alpha

Acute hepatic inflammation is regarded as a hallmark of early stage fibrosis, which can progress to extensive fibrosis and cirrhosis. Sinapic acid is a phenylpropanoid compound that is abundant in cereals, nuts, oil seeds, and berries and has been reported to exhibit a wide range of pharmacological properties. In this study, we investigated the anti-inflammatory effect of sinapic acid in carbon tetrachloride (CCl4)-induced acute hepatic injury in rats. Sinapic acid was administered orally (10 or 20 mg/kg) to rats at 30 min and 16 h before CCl4 intoxication. Sinapic acid treatment of rats reduced CCl4-induced abnormalities in liver histology, serum alanine transaminase and aspartate transaminase activities, and liver malondialdehyde levels. In addition, sinapic acid treatment significantly attenuated the CCl4-induced production of inflammatory mediators, including tumor necrosis factor-alpha and interleukin-1β mRNA levels, and increased the expression of nuclear factor-kappa B (NF-κB p65). Sinapic acid exhibited strong free radical scavenging activity in vitro. Thus, sinapic acid protected the rat liver from CCl4-induced inflammation, most likely by acting as a free radical scavenger and modulator of NF-κB p65 activation and proinflammatory cytokine expression. Sinapic acid may thus have potential as a therapeutic agent for suppressing hepatic inflammation.

Topics: Acute Disease; Animals; Anti-Inflammatory Agents; Biphenyl Compounds; Blotting, Western; Body Weight; Carbon Tetrachloride; Chemical and Drug Induced Liver Injury; Coumaric Acids; Disease Models, Animal; Free Radical Scavengers; Interleukin-1beta; Lipid Peroxidation; Liver; Liver Function Tests; Male; Molecular Structure; Organ Size; Picrates; Rats; Rats, Sprague-Dawley; Reverse Transcriptase Polymerase Chain Reaction; Transcription Factor RelA; Transforming Growth Factor beta1

Phenolic composition and antioxidant activities of the aqueous extract of Arisaema cum Bile, which is widely used as a folk medicine in Korea, were determined. Phenolic composition profile revealed that the aqueous extract is rich in sinapic acid (13.14 mg/100 g extract), catechin (9.88 mg/100 g extract), neohesperidin (7.38 mg/100 g extract), and chlorogenic acid (3.64 mg/100 g extract). The aqueous extract effectively scavenged toward 2,2-diphenyl-1-picrylhydrazyl (90.63%), hydrogen peroxide (98.13%), and hydroxyl radical (59.62%) at 2.0 mg/mL, and also showed high reducing power. In cytotoxic evaluation, the aqueous extract exhibited no significant cytotoxicity in human fibroblast, and it also exhibited appreciable suppression of intracellular reactive oxygen species and inhibition of lipid peroxidation. In addition, the aqueous extract upregulated the level of glutathione in a dose-dependent manner. Taken together, the aqueous extract of Arisaema cum Bile could be considered as a potential natural source that may be useful for curing diseases arising from oxidative deterioration.

Topics: Anti-Infective Agents; Antioxidants; Arisaema; Biphenyl Compounds; Cell Line; Complex Mixtures; Coumaric Acids; Dose-Response Relationship, Drug; Fibroblasts; Humans; Hydrogen Peroxide; Hydroxyl Radical; Oxidation-Reduction; Picrates

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