High Concentrations Of Ferulic Acid Research Articles

Effects of Dietary Supplementation with a Ferulic Acid-Rich Bioactive Component of Wheat Bran in a Murine Model of Graft-Versus-Host Disease.

Graft-versus-host disease (GvHD) is a common and severe complication following allogeneic hematopoietic stem cell transplantation (HSCT). Its prevention and treatment is a major challenge. Ferulic acid (FA) has anti-inflammatory and antioxidant properties that could be attractive in this setting. Our aim was to evaluate a bioactive ingredient derived from wheat bran (WB), selected for its high concentration of FA, in a murine model of GvHD. The ingredient was obtained via a bioprocess involving hydrolysis and spray-drying. GvHD was induced via HSCT between MHC-mismatched mouse strains. FA treatment was administered orally. Survival and disease scores (weight loss, hunching, activity, fur texture, and skin integrity, each scored between 0 and 2 depending on disease severity) were recorded daily, histological evaluation was performed at the end of the experiment, and serum inflammatory cytokines were analyzed on days 9 and 28. Treatment with FA did not protect GvHD mice from death, nor did it diminish GvHD scores. However, histological analysis showed that ulcers with large areas of inflammatory cells, vessels, and keratin were less common in skin samples from FA-treated mice. Areas of intense inflammatory response were also seen in fewer small intestine samples from treated mice. In addition, a slight decrease in INF-γ and TNF-α expression was observed in the serum of treated mice on day 28. The results showed some local effect of the ingredient intervention, but that the dose used may not be sufficient to control or reduce the inflammatory response at the systemic level in mice with GvHD. Higher dosages of FA may have an impact when evaluating the immunomodulatory capabilities of the hydrolyzed WB ingredient. Thus, further experiments and the use of technological strategies that enrich the ingredients in soluble ferulic acid to improve its efficacy in this setting are warranted.

Hydroxylated Cinnamates Enhance Tomato Resilience to Alternaria alternata, the Causal Agent of Early Blight Disease, and Stimulate Growth and Yield Traits.

The important vegetable crop, tomato, is challenged with numerous abiotic and biotic stressors, particularly the newly emerged fungicide-resistant strains of phytopathogenic fungi such as Alternaria alternata, the causal agent of early blight disease. The current study investigated the potential antifungal activity of four cinnamate derivatives including cinnamic acid, ρ-coumaric acid, caffeic acid, and ferulic acid against A. alternata. Our in vitro findings showed that all tested compounds exhibited dose-dependent fungistatic action against A. alternata when their concentrations were increased from 0.1, 0.3, 0.5, and 0.7, to 0.9 mM, respectively. The high concentration of ferulic acid (0.9 mM) completely inhibited the radial mycelial growth of A. alternata and it was comparable to the positive control (difenoconazole fungicide). Additionally, under greenhouse conditions, foliar application of the four tested cinnamates significantly reduced the severity of early blight disease without any phytotoxicity on treated tomato plants. Moreover, it significantly improved the growth traits (plant height, total leaf area, number of leaves per plant, and shoot fresh weight), total chlorophyll, and yield components (number of flowers per plant, number of fruits per plant, and fruit yield) of treated A. alternata-infected plants. Collectively, our findings suggest that cinnamate derivatives could be good candidates as eco-friendly alternatives to reduce the use of chemical fungicides against A. alternata.

Theoretical Study of Radical Inactivation, LOX Inhibition, and Iron Chelation: The Role of Ferulic Acid in Skin Protection against UVA Induced Oxidative Stress.

Ferulic acid (FA) is used in skin formulations for protection against the damaging actions of the reactive oxygen species (ROS) produced by UVA radiation. Possible underlying protective mechanisms are not fully elucidated. By considering the kinetics of proton-coupled electron transfer (PCET) and radical-radical coupling (RRC) mechanisms, it appears that direct scavenging could be operative, providing that a high local concentration of FA is present at the place of •OH generation. The resulting FA phenoxyl radical, after the scavenging of a second •OH and keto-enol tautomerization of the intermediate, produces 5-hydroxyferulic acid (5OHFA). Inhibition of the lipoxygenase (LOX) enzyme, one of the enzymes that catalyse free radical production, by FA and 5OHFA were analysed. Results of molecular docking calculations indicate favourable binding interactions of FA and 5OHFA with the LOX active site. The exergonicity of chelation reactions of the catalytic Fe2+ ion with FA and 5OHFA indicate the potency of these chelators to prevent the formation of •OH radicals via Fenton-like reactions. The inhibition of the prooxidant LOX enzyme could be more relevant mechanism of skin protection against UVA induced oxidative stress than iron chelation and assumed direct scavenging of ROS.

Adaptive laboratory evolution of Pseudomonas putida KT2440 improves p-coumaric and ferulic acid catabolism and tolerance

Pseudomonas putida KT2440 is a promising bacterial chassis for the conversion of lignin-derived aromatic compound mixtures to biofuels and bioproducts. Despite the inherent robustness of this strain, further improvements to aromatic catabolism and toxicity tolerance of P. putida will be required to achieve industrial relevance. Here, tolerance adaptive laboratory evolution (TALE) was employed with increasing concentrations of the hydroxycinnamic acids p-coumaric acid (pCA) and ferulic acid (FA) individually and in combination (pCA ​+ ​FA). The TALE experiments led to evolved P. putida strains with increased tolerance to the targeted acids as compared to wild type. Specifically, a 37 ​h decrease in lag phase in 20 ​g/L pCA and a 2.4-fold increase in growth rate in 30 ​g/L FA was observed. Whole genome sequencing of intermediate and endpoint evolved P. putida populations revealed several expected and non-intuitive genetic targets underlying these aromatic catabolic and toxicity tolerance enhancements. PP_3350 and ttgB were among the most frequently mutated genes, and the beneficial contributions of these mutations were verified via gene knockouts. Deletion of PP_3350, encoding a hypothetical protein, recapitulated improved toxicity tolerance to high concentrations of pCA, but not an improved growth rate in high concentrations of FA. Deletion of ttgB, part of the TtgABC efflux pump, severely inhibited growth in pCA ​+ ​FA TALE-derived strains but did not affect growth in pCA ​+ ​FA in a wild type background, suggesting epistatic interactions. Genes involved in flagellar movement and transcriptional regulation were often mutated in the TALE experiments on multiple substrates, reinforcing ideas of a minimal and deregulated cell as optimal for domesticated growth. Overall, this work demonstrates increased tolerance towards and growth rate at the expense of hydroxycinnamic acids and presents new targets for improving P. putida for microbial lignin valorization.

High concentration of ferulic acid in rhizosphere soil accounts for the occurrence of Fusarium wilt during the seedling stages of strawberry plants

Here, we elucidated the relationship between phenolic acids in strawberry rhizosphere soil and the occurrence of Fusarium wilt. Ten phenolic acids were identified, and the concentration of ferulic acid (FA) in the rhizosphere was higher than other phenolic acids at the seedling stage of strawberry plants. Treatment with relatively high FA concentrations enhanced the conidial germination and colony growth of Fusarium oxysporum in vitro. Exogenous supplementation with FA increased the disease index of Fusarium wilt. Our results suggest the key role of high concentrations of FA in rhizosphere soil in the occurrence of strawberry Fusarium wilt during the seedling stage.

Allelopathic effects of phenolic acids on seedling growth and photosynthesis in Rhododendron delavayi Franch.

The effects of different concentrations of ferulic acid, chlorogenic acid, and protocatechuic acid were studied in a pot experiment to assess the response of Rhododendron delavayi seedlings. The results showed that three kinds of phenols promoted increases in chlorophyll (Chl) a, Chl b, total Chl, and carotenoid contents, but inhibited the accumulation of biomass. Low concentrations of ferulic acid significantly inhibited stomatal opening, the stomatal opening ratio, stomatal length and width. Chlorogenic acid and the moderate and high concentrations of ferulic acid also significantly inhibited stomatal density. Ferulic acid significantly inhibited net photosynthetic rate and stomatal conductance in seedlings, whereas chlorogenic acid significantly inhibited stomatal conductance. The low and moderate concentrations of chlorogenic acid significantly inhibited transpiration rate, and high concentrations of ferulic acid significantly inhibited the stomatal limitation value. The moderate concentration of protocatechuic acid significantly inhibited net photosynthetic rate and stomatal conductance. Ferulic acid exhibited a greater toxic effect than that of chlorogenic acid and protocatechuic acid for R. delavayi seedlings.

Phenolic acids in the plow layer soil of strawberry fields and their effects on the occurrence of strawberry anthracnose

Phenolic allelochemicals have been found in both natural and managed ecosystems, where they cause numerous ecological and economic problems. Whether these problems can be mediated by some other specific phenolic acid components is unknown. In this study, we identified phenolic acids and their concentrations in plow layer soil, rhizosphere soil and decomposing strawberry (Fragaria ananassa Duch.‘Benihoppe’.) plants susceptible to strawberry anthracnose crown rot. We also assessed the effects of exogenously added phenolic acids at varying concentrations on Colletotrichum gloeosporioides, the pathogen causing strawberry anthracnose crown rot, conidial germination and colony growth. Finally, we verified the occurrence of strawberry anthracnose crown rot and the changes in root structure in response to phenolic acids. Ten phenolic acids were identified in soil samples. The concentrations of p-coumaric acid (PA) and ferulic acid (FA) were higher than other phenolic acids. Relatively high concentrations of PA and FA could increase the occurrence of strawberry seedling anthracnose crown rot. However, when the concentrations of PA and FA were higher than respectively certain critical concentration, they could reduce the degree of the disease. Meanwhile, high concentration of FA seriously inhibited the growth of root. The trans-cinnamic acid (TA) content could be regulated to control the occurrence of strawberry anthracnose crown rot without affecting root growth. Overall, diverse phenolic acids in plow soil had different influence on strawberry anthracnose crown rot. The effects of phenolic acids were concentration-dependent and C. gloeosporioides was more sensitive to phenolic acids concentration than root.

Identification of Phenolic Compounds and Evaluation of Antioxidant and Antimicrobial Properties of Euphorbia Tirucalli L.

Bioactive compounds extracted from natural sources can benefit human health. The aim of this work was to determine total phenolic content and antioxidant activity in extracts of Euphorbia tirucalli L. followed by identification and quantification of the phenolic compounds, as well as their antibacterial activities. Antioxidant activities were determined by DPPH and ABTS•+ assay. Identification of phenolic compounds was performed using high-performance liquid chromatography (HPLC), and antimicrobial activities were verified by agar dilution methods and MIC values. Total phenolic content ranged from 7.73 to 30.54 mg/100 g gallic acid equivalent. Extracts from dry plants showed higher antioxidant activities than those from fresh ones. The DPPH EC50 values were approximately 12.15 μg/mL and 16.59 μg/mL, respectively. Antioxidant activity measured by the ABTS method yielded values higher than 718.99 μM trolox/g for dry plants, while by the Rancimat® system yielded protection factors exceeding 1 for all extracts, comparable to synthetic BHT. Ferulic acid was the principal phenolic compound identified and quantified through HPLC-UV in all extracts. The extracts proved effective inhibitory potential for Staphylococcus epidermidis and Staphylococcus aureus. These results showed that extracts of Euphorbia tirucalli L. have excellent antioxidant capacity and moderate antimicrobial activity. These can be attributed to the high concentration of ferulic acid.

Effect of bioconversion conditions on vanillin production by Amycolatopsis sp. ATCC 39116 through an analysis of competing by-product formation

This study investigated the effects of transformation conditions such as initial pH, the initial concentration of glucose and yeast extract in the medium, and the separate addition of ferulic acid and vanillic acid, on the production of vanillin through an analysis of competing by-product formation by Amycolatopsis sp. ATCC 39116. The extent and nature of by-product formation and vanillin yield were affected by initial pH and different initial concentrations of glucose and yeast extract in the medium, with a high yield of vanillin and high cell density obtained at pH 8.0, 10 g/l glucose, and 8 g/l yeast extract. High concentrations of ferulic acid were found to negatively affect cell density. Additional supplementation of 100 mg/l vanillic acid, a metabolically linked by-product, was found to result in a high concentration of vanillin and guaiacol, an intermediate of vanillin. Via an analysis of the effect of these transformation conditions on competing by-product formation, high concentrations of ferulic acid were transformed with a molar yield to vanillin of 96.1 and 95.2 %, by Amycolatopsis sp. ATCC 39116 and Streptomyces V1, respectively, together with a minor accumulation of by-products. These are among the highest performance values reported in the literature to date for Streptomyces in batch cultures.

Effects of toasting on the carbohydrate profile and antioxidant properties of chickpea (Cicer arietinum L.) flour added to durum wheat pasta

The effects of the toasting process on the carbohydrate profile and antioxidant properties of chickpea flour were studied, along with the cooking behaviour, and antioxidant and nutritional properties of pasta enriched with the chickpea flour. The toasting process increased the resistant starch, insoluble dietary fibre and antioxidant properties of the flour. Addition of chickpea flour (raw and toasted) to durum wheat semolina changed the carbohydrate profile in the uncooked and cooked enriched pasta, especially with the toasted chickpea, and worsened the overall quality of the pasta. The increase in total phenolic content and total free phenolic acid content in the uncooked pasta was due to positive effects of addition of the chickpea flours, while the increase in the bound phenolics fraction in the cooked pasta was from the durum wheat, which was crucial for its high concentrations of ferulic acid. The increase in the free fraction of the Trolox equivalent antioxidant capacity in cooked pasta was consistent with the addition of chickpea.

Effect of natural maize phytochemicals on Aspergillus section Flavi sclerotia characteristics under different conditions of growth media and water potential

Abstract The effects of the natural phytochemicals trans-cinnamic acid (CA) and ferulic acid (FA) at concentrations of 1–20 mM (CA) and 1–25 mM (FA) on sclerotial production by Aspergillus flavus and Aspergillus parasiticus were evaluated. Studies on sclerotium number and size were carried out in different growth media and water potentials (MPa). High concentrations of CA (20 mM, −0.75 MPa; 10 mM, −3.5 MPa) and FA (10, 20, 25 mM, −0.75 and −3.5 MPa) significantly reduced sclerotial production of Aspergillus strains. Overall, CA at concentrations of 10 and 20 mM on Czapek Dox medium (CD), maize meal extract agar (MMEA) and maize meal extract agar with sucrose and NaNO3 (MMEA S/N) inhibited sclerotium most in the four species assayed. The data show that the sclerotia characteristics of A. flavus and A. parasiticus were influenced by natural phytochemicals and modifications of growth media and water potential. CA and FA could be used at high concentrations to prevent the survival of Aspergillus species in grain.

Enhanced vanillin production from ferulic acid using adsorbent resin

High vanillin productivity was achieved in the batch biotransformation of ferulic acid by Streptomyces sp. strain V-1. Due to the toxicity of vanillin and the product inhibition, fed-batch biotransformation with high concentration of ferulic acid was unsuccessful. To solve this problem and improve the vanillin yield, a biotransformation strategy using adsorbent resin was investigated. Several macroporous adsorbent resins were chosen to adsorb vanillin in situ during the bioconversion. Resin DM11 was found to be the best, which adsorbed the most vanillin and the least ferulic acid. When 8% resin DM11 (wet w/v) was added to the biotransformation system, 45 g l(-1) ferulic acid could be added continually and 19.2 g l(-1) vanillin was obtained within 55 h, which was the highest vanillin yield by bioconversion until now. This yield was remarkable for exceeding the crystallization concentration of vanillin and therefore had far-reaching consequence in its downstream processing.

Genetic and Agronomic Variation in Arabinoxylan and Ferulic Acid Contents of Durum Wheat (Triticum durumL.) Grain and Its Milling Fractions

Total arabinoxylan (AXt), water-extractable arabinoxylan (WeAX) and ferulic acid (FA) from five cultivars of durum wheat ( Triticum durum L.), grown under four different agronomic conditions, were measured. Among the varieties analysed, AXt, WeAX and FA contents ranged between 4·07%–6·02%, 0·37%–0·56% and 0·784 mg/g–7·98 mg/g, respectively. High genetic and agronomic variability was detected for AXt, WeAX and FA. AXt and FA increased sharply in milling products for extraction rates above 60%. FA was quantified in durum wheat milling fractions. High concentrations of FA esterified to cell-wall arabinoxylans were found in the aleurone layer (69% of total FA), germ and seedcoat (26·6% of total FA). Only trace amounts were detected in the starchy endosperm (1·4% of total FA). A highly significant correlation appeared between AXt and FA contents.

The Characterization of a Lignin-Derived Organic Matter Fraction in Soils Developed Under Different Vegetation Types

1. Soil profiles developed under beech woodland, spruce woodland, pasture and arable cropping were analysed for total organic C and lignin derivatives extracted by CuO oxidation. This reaction primarily releases lignin-derived phenylpropanoid moieties from soil organic matter(SOM). The amount and composition of the moieties obtained provided a signature that was related to the origin of organic matter from particular soil horizons. 2. There were clear differences between the lignin-derived phenylpropanoid signatures from similar depth horizons of soils developed under beech, spruce and pasture. This was characterized by: equal amounts of syringyl and vanillyl residues; a low syringyl:vanillyl ratio; and high concentration of ferulic acid, respectively, in the surface soil layers. The arable soil profile showed little differentiation in phenylpropanoid signature with depth (0-18 cm), presumably because of annual tillage. 3. Further investigation into the degradation rates of individual phenylpropanoid moieties in soils and their adsorption onto soil fractions is required. A more extensive survey, characterizing the 'lignin'-derived fraction in soils with a well documented land use history is also needed to establish a time scale for the translocation and degradation of the phenylpropanoid signatures of soils. Once calibrated, however, temporal changes in the composition of the lignin-phenylpropanoid SOM fraction will be potentially useful in monitoring the effects of vegetation and land management change on soil C cycling.

Spore germination and germ hyphal growth of microfungi from litter and soil in the presence of ferulic acid

Ferulic acid, a phenolic acid related to lignin, was incorporated into water agar for studies on its effect on the germination of spores of fungi representing several ecological groups from litter and soil. Ferulic acid could inhibit or stimulate germination and hyphal growth, the response of the fungus depending upon its ecological distribution and the concentration of the acid. Soilinhabiting species such as Penicillium spp. and conifer needle saprophytes such as Dothichiza pityophila (Corda) Petrak and Thysanophora penicillioides (Roum.) Kendrick showed stimulation of germination, the latter at high concentrations of ferulic acid, whereas Angiosperm leaf saprophytes were significantly depressed. These results suggest that some soil and conifer litter species show an important adaptation to the presence of this compound, and possibly other similar substances, in the environment.