linoleic-acid and ferulic-acid

Novel phosphatidylcholines containing PUFAs and phenolic acids were synthesized from egg phosphatidylcholine (PC), PUFAs (docosahexaenoic, arachidonic and linoleic acids) and phenolic acids (caffeic, ferulic and p-coumaric acids) as substrates. The structures of modified PCs were confirmed by spectral analysis and were evaluated for antioxidant activities. The modified PCs containing caffeic and ferulic acids exhibited excellent antioxidant activities compared with butylated hydroxytoluene (BHT) and α-tocopherol. The synthesized compounds were also evaluated for the oxidative stabilities in liposome and organic solvent. The modified PCs showed more oxidative stable compared with standard PUFA-PCs and PUFA-PCs + BHT. Results showed that the oxidative stability decreased with increasing degree of unsaturation in organic solvent whereas in liposomes, increased with increasing degree of unsaturation due to tight packed configuration. In this study, phenolic acids were found to render protections for PUFAs in modified PCs from oxidation. Modified PCs may have great potential for applications in food, cosmetic and pharmaceutical industries.

Topics: alpha-Tocopherol; Antioxidants; Butylated Hydroxytoluene; Coumaric Acids; Fatty Acids, Omega-3; Fatty Acids, Omega-6; Fatty Acids, Unsaturated; Hydroxybenzoates; Linoleic Acid; Liposomes; Oxidation-Reduction; Oxidative Stress; Phosphatidylcholines

Huitlacoche mushroom (composed by the fruiting bodies growing on the maize ears from the basidiomycete Ustilago maydis) is a culinary delicacy with a great economic and nutraceutical value. In this work, phenolic content, antioxidant activity, ergosterol and fatty acids profile from huitlacoche produced in 15 creole and in one hybrid maize genotypes, and harvested at different stages of development were determined. The hybrid crop was studied in raw and cooked samples. Total phenolic content ranged from 415.6 to 921.8.0 mg gallic acid equivalents per 100 g of flour. Samples exhibited attractive antioxidant activities: 75 % of antiradical activity on average by DPPH methodology, and ORAC values up to 7661.3 μmol Trolox equivalents /100  g. Important quantities of ferulic acid, quercetin, ergosterol, linoleic and oleic acids were observed. Stage of development and cooking process had an effect on evaluated compounds, sometimes negative and sometimes positive. Results suggest that huitlacoche is an attractive food source of phenolics with excellent antioxidant potential and interesting lipidic compounds.

Topics: Agaricales; Antioxidants; Coumaric Acids; Ergosterol; Fatty Acids; Food Handling; Gallic Acid; Genotype; Linoleic Acid; Oleic Acid; Phenols; Quercetin; Ustilago; Zea mays

In this study, ten different phenolic acids (caffeic, chlorogenic, cinnamic, ferulic, gallic, p-hydroxybenzoic, protocatechuic, rosmarinic, syringic, and vanillic acids) were evaluated for their antioxidant and DNA damage protection potentials. Antioxidant activity was evaluated by using four different test systems named as β-carotene bleaching, DPPH free radical scavenging, reducing power and chelating effect. In all test systems, rosmarinic acid showed the maximum activity potential, while protocatechuic acid was determined as the weakest antioxidant in β-carotene bleaching, DPPH free radical scavenging, and chelating effect assays. Phenolic acids were also screened for their protective effects on pBR322 plasmid DNA against the mutagenic and toxic effects of UV and H2O2. Ferulic acid was found as the most active phytochemical among the others. Even at the lowest concentration value (0.002 mg/ml), ferulic acid protected all of the bands in the presence of H2O2 and UV. It is followed by caffeic, rosmarinic, and vanillic acids. On the other hand, cinnamic acid (at 0.002 mg/ml), gallic acid (at 0.002 mg/ml), p-hydroxybenzoic acid (at 0.002 and 0.004 mg/ml), and protocatechuic acid (at 0.002 and 0.004 mg/ml) could not protect plasmid DNA.

Topics: Antioxidants; beta Carotene; Cinnamates; Coumaric Acids; Depsides; DNA Damage; Gallic Acid; Hydrogen Peroxide; Hydroxybenzoates; Linoleic Acid; Phytochemicals; Rosmarinic Acid; Ultraviolet Rays; Vanillic Acid

The metabolic changes of bacterial blight-resistant line C418/Xa23 generated by molecular marker-assisted selection (n= 12), transgenic variety C418-Xa21 generated by using the Agrobacterium-mediated system (n= 12), and progenitor cultivar C418 (n= 12) were monitored using gas chromatography/mass spectrometry. The validation, discrimination, and establishment of correlative relationships between metabolite signals were performed by cluster analysis, principal component analysis, and partial least squares-discriminant analysis. Significant and unintended changes were observed in 154 components in C418/Xa23 and 48 components in C418-Xa21 compared with C418 (P< 0.05, Fold change > 2.0). The most significant decreases detected (P< 0.001) in both C418/Xa23 and C418-Xa21 were in three amino acids: glycine, tyrosine, and alanine, and four identified metabolites: malic acid, ferulic acid, succinic acid, and glycerol. Linoleic acid was increased specifically in C418/Xa23 which was derived from traditional breeding. This line, possessing a distinctive metabolite profile as a positive control, shows more differences vs. the parental than the transgenic line. Only succinic acid that falls outside the boundaries of natural variability between the two non-transgenic varieties C418 and C418/Xa23 should be further investigated with respect to safety or nutritional impact.

Topics: Alanine; Biotechnology; Coumaric Acids; Gas Chromatography-Mass Spectrometry; Glycerol; Least-Squares Analysis; Linoleic Acid; Malates; Metabolomics; Models, Genetic; Oryza; Plant Diseases; Plant Proteins; Plants, Genetically Modified; Principal Component Analysis; Succinic Acid; Transgenes; Tyrosine

To study the chemical constituents of the root and rhizoma of Ligusticum jeholense.. The constituents were isolated by silica gel column chromatography, Sephadex LH-20 column chromatography and their structures were elucidated through spectral analysis.. Seven compounds were separated from the EtOH extracts. Their structures were identified as levistolide A (1), xiongterpene (2), linoleic acid (3), sucrose (4), daucosterol (5), ferulic acid (6) and beta-sitosterol (7).. Compounds 1-5 are isolated from the genus for the first time.

Topics: Benzofurans; Coumaric Acids; Ligusticum; Linoleic Acid; Molecular Structure; Plant Roots; Plants, Medicinal; Rhizome; Sitosterols; Sucrose; Terpenes

The oxidation processes of linoleic acid in the presence of ferulic acid, and 1-pentyl, 1-hexyl and 1-heptyl ferulates were observed at various temperatures and different molar ratios of each additive to linoleic acid. The processes were analyzed based on a kinetic equation of the autocatalytic type to evaluate the oxidative rate constant, k, and the kinetic parameter, Y(0), by which the initiation period for the oxidation of linoleic acid was mainly governed. The k values for linoleic acid mixed with each of the alkyl ferulates were smaller than that for linoleic acid mixed with ferulic acid. The greater suppressive effect of the alkyl ferulates would be ascribable to their higher solubility in linoleic acid. Both the activation energy, E, and the frequency factor, k(0), for the oxidation of linoleic acid mixed with ferulic acid or pentyl ferulate decreased with increasing molar ratio of the additive to linoleic acid.

Topics: Alkylation; Catalysis; Coumaric Acids; Kinetics; Linoleic Acid; Oxidation-Reduction; Solubility

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