Effect Of Hydroxycinnamic Acids Research Articles

An in vitro evaluation of the effect of hydroxycinnamic acids on the growth and hydrolytic enzyme production in Fusarium oxysporum f. sp. albedinis

Activation of the phenylpropanoids pathway in date palm (Phoenix dactylifera L.) roots is a key defense mechanism against Fusarium oxysporum f. sp. albedinis (Foa), the causal agent of bayoud. In this study, the effects of four hydroxycinnamic acids (0-5 µm/ml), mainly caffeic acid, p-coumaric acid, ferulic acid and sinapic acid, on fungal biomass production, sporulation and hydrolytic enzymes (protease, cellulase, polygalacturonase and pectinemethyl-esterase) of Foa were investigated. In vitro tests results showed an overall inhibition effect of caffeic and p-coumaric acids compared to ferulic and sinapic acids. Caffeic and p-coumaric acids at 5 µmol/ml had highest inhibition rates of mycelial growth and sporulation ranging from 73 to 80% and 97 to 100%, respectively. For hydrolytic enzyme activities, the inhibition rate of hydoxycinnamic acids tested for protease ranged from 80 to 100%, 63 to 98% for cellulase, 91 to 100% for pectinemethyl-esterase and 59 to 99% for polygalacturonase. Nevertheless, it was found that sinapic acid, at low concentration (0.5 µmol/ml), has no inhibition effect on mycelial growth and hydrolytic enzyme activities. Additionally, the half maximal inhibitory concentration (IC50) has also been determined to compare the different acids effects.

Efficiency of Hydroxycinnamic Phenolic Acids to Inhibit the Production of Ochratoxin A by Aspergillus westerdijkiae and Penicillium verrucosum.

Ochratoxin A (OTA) is one of the worldwide most important mycotoxins in terms of health and agroeconomic consequences. With the aim to promote the use of phytochemicals as alternatives to synthetic fungicides, the effect of hydroxycinnamic acids on the fungal growth and OTA yield by two major OTA-producing species was investigated. After a first step dedicated to the definition of most suitable culture conditions, the impact of 0.5 mM ferulic (FER), p-coumaric (COUM), caffeic and chlorogenic acids was evaluated on Aspergillus westerdijkiae and Penicillium verrucosum. Whereas no fungal growth reduction was observed regardless of the phenolic acid and fungal isolate, our results demonstrated the capacity of FER and COUM to inhibit OTA production. The most efficient compound was FER that led to a 70% reduction of OTA yielded by P. verrucosum and, although not statistically significant, a 35% inhibition of OTA produced by A. westerdijkiae. To further investigate the bioactivity of FER and COUM, their metabolic fate was characterized in fungal broths. The capacity of P. verrucosum to metabolize FER and COUM through a C2-clivage type degradation was demonstrated. Overall, our data support the potential use of FER to prevent OTA contamination and reduce the use of synthetic pesticides.

Effects of hydroxycinnamic acids on the reduction of furan and α-dicarbonyl compounds

The effects of hydroxycinnamic acids such as cinnamic acid (CNA), p-coumaric acid(CMA), caffeic acid (CFA), and chlorogenic acid (CGA) on the reduction of furan in canned-coffee model systems (CCMS) containing α-dicarbonyls [glyoxal (GO) or methylglyoxal (MGO)] were investigated. The concentration of furan in CCMS containing GO, which was 59.76 μg/L, was reduced by the addition of CFA and CGA to 48.31 μg/L and 41.38 μg/L, respectively; similarly, the furan concentration in model system containing MGO was 45.79 μg/L, and this decreased to 35.41 μg/L (by CFA) and 32.65 μg/L (by CGA), respectively. In addition, the effects of hydroxycinnamic acids on the trapping of GO and MGO were determined. CFA and CGA greatly reduced the concentration of GO to 303.51 μg/L and 267.80 μg/L, respectively (compared to 515.79 μg/L in the control), whereas that of MGO was decreased to 207.01 μg/L and 219.14 μg/L (compared to 417.14 μg/L in the control). The trapping of α-dicarbonyls such as GO and MGO by CFA and CGA could be closely related to furan reduction in CCMS.

Effects of hydroxycinnamic acids on the glycolysis pathway

Glycolysis is a metabolic pathway vital to the production of energy and some organisms rely on it solely to meet their energy requirements. It is also a central pathway in the metabolism of carbohydrates and a source of therapeutic targets against diabetes and cancer. Caffeoylquinic acids (CQAs) have been extensively studied for their role in the treatment and prevention of diabetes (and cancer) but their mechanisms of action remain mostly unknown. As such, molecular docking was used to find possible targets of CQAs in the glycolysis pathway. The molecular docking assays showed that CQAs were docked preferably to the Rossman fold (nicotinamide adenine dinucleotide — NAD(H) binding site) of oxidoreductases, that use NAD(H) as a cofactor, than to any other site. In-vitro assays were then performed using two NAD(H) dependent oxidoreductases from glycolysis (alcohol dehydrogenase and L-lactate dehydrogenase) in order confirm if CQAs would compete with the cofactor to inhibit the reaction. The results from these assays indicate that CQAs can act as both inhibitors and activators of NAD(H) dependent oxidoreductases of the glycolysis pathway.

Effects of hydroxycinnamic acids (Ferulic and p-coumaric acids) in barley cultivars on cell wall components degradability in rumen

Barley grain contains hydroxycinnamic acids especially Ferulic (FA) and p-Coumaric acid (pCA) become cross-linked to cell wall polysaccharids as lignification commences that are the major inhibiting factors of biodegradability of plant cell walls in the rumen. Chemical characteristics, FA and pCA content of 11 Iranian barley cultivars determined. Using 3 fistulated ewes, the effects of FA and pCA content on ruminal degradation of dry matter (DM), neutral and acid detergent fiber (NDF and ADF) and lignin were studied. In barley cultivars, DM varied from 82.52 to 90.90 %; NDF varied from 9.64 to 27.34 % DM; ADF varied from 2.03 to 8.13 % DM and lignin varied from 0.87 to 3.03 % DM. The FA content ranged from 151.2 to 354.2 ?g/g; and pCA content ranged from 114.5 to 444.4 ?g/g of DM. Ruminal degradation parameters for DM, NDF, ADF and lignin were different between barley cultivars. The soluble fraction, slowly degradable, potential degradable, and undegradable fraction of DM were 2.92 to 56.33%; 42.64 to 91.45%; 65.68 to 98.97%, and 1.02 to 34.31%, respectively. The rate of ruminal degradation for DM varied among barley cultivars from 3.64 to 27.81% h-1. The FA was related to rumen indigestible DM, NDF, ADF and lignin, while pCA correlated with ADF. Using multi-regression, FA and pCA were inhibiting factors of ruminal degradability for DM and cell wall components; and FA was the most effective factor to predict DM degradability, while both FA and pCA affected NDF and ADF ruminal degradability.

The Effect of Hydroxycinnamic Acids on Oxy-Radical Generating Iodide–Hydrogen Peroxide Reaction

Abstract The influence of hydroxycinnamic acids (HCA) on the oxy-radical generated system, potassium iodide/hydrogen peroxide, was investigated through the enhancement of triiodide (I3−) yield. Caffeic acid, chlorogenic acid, and p-coumaric acid were used as typical representatives of HCA. A linear correlation, with positive slopes, was found between absorption maximum of I3− at 351 nm and HCA concentration in all cases. The magnitude of enhanced I3− production was found to increase in the following order: p-coumaric acid < chlorogenic acid ≤ caffeic acid. A reaction mechanism, which includes negative influence of oxygen-centered free radicals on the I3− yield, was proposed. The enhanced production of I3− by HCA is attributed to their radical scavenging activity. Supported by literature data, results obtained in this study have showed the correlation between radical scavenging activities of HCA and their ability to enhanced I3− generation.

Effect of hydroxycinnamic acids on lipid oxidation and protein changes as well as water holding capacity in frozen minced horse mackerel white muscle

The antioxidant effectiveness of different hydroxycinnamic acids for inhibiting the formation of off-flavours associated to rancidity in minced frozen horse mackerel white muscle stored at −10 and −18 °C was studied. The influence of lipid oxidation on protein aggregation, protein denaturation and water holding capacity was also determined. Caffeic acid, o-coumaric acid and ferulic acid were the antioxidants tested. The order of antioxidant effectiveness was caffeic acid > ferulic acid > o-coumaric acid accordingly with previous results obtained in chilled horse mackerel. A strong dependence of antioxidant effectiveness to the ratio lipid/antioxidant concentration was observed. There was no evidence to suggest that antioxidants reduce protein aggregation or water holding capacity changes. Protein aggregation was not accompanied by gross protein denaturation, as monitored by differential scanning calorimetry. No evidence was found for a link between extent of lipid oxidation and degree of protein aggregation or water holding capacity changes.

The Effect of Hydroxycinnamic Acids and Volatile Phenols on Beer Quality

To the consumer, beer should be an agreeable beverage of attractive colour, clarity, pleasing flavour and should carry no toxic substances. One of the major constituents of barley is phenolic acids and their direct effect on the quality of beer is still a mystery. The aim of the study therefore was to investigate the relationship between phenolic acids during mashing at different temperatures and the quality of the beer. The mash regime and liquor to malt ratios were optimised and the carbohydrates obtained were analysed at 3.5 L of water per kg of malt and a total mash time of 105 min. Carbohydrate and phenolic acid analyses were performed by HPLC coupled with a UV-vis detector. The three different malts used had a phenolic acid content of 33.25 μg/mL, 25.44 μg/mL and 19.98 μg/mL for malt A, B and C, respectively. The plot of 1/T versus Ln(t) gave a negative slope with activation energy (Ea) = 209 KJ/mol, rate constant (k) = 4.6 × 10−4 mg/L min, which are comparable to similar data reported in the literature. The kinetics studies showed that the optimised mashing temperature of 90°C was adequate to form 4-vinylguaiacol by thermal decarboxylation from the hydroxycinnamic acids. This study has shown that there is no direct correlation between phenolic acids and oxidative flavour stability of beer while the corresponding volatile phenols may affect beer flavour.

The effect of hydroxycinnamic acids and potassium sorbate on the growth of 11 strains of spoilage yeasts

Hydroxycinnamic acids and their derivatives occur widely in plants, fruits and wine. The effect of the common hydroxycinnamic acids (caffeic, coumaric and ferulic acids), at concentrations of 100 and 500 mg l-1, on growth of 11 strains of spoilage yeasts was measured spectrophotometrically and compared with that of potassium sorbate. Ferulic acid was the most generally inhibitory hydroxycinnamic acid. At 500 mg l-1 it appreciably inhibited Pichia anomala, Debaryomyces hansenii and Saccharomyces cerevisiae and prevented detectable growth of one strain each of P. anomala and D. hansenii. Caffeic acid was the least inhibitory compound and coumaric acid had an intermediate effect. The more resistant strains of yeast were P. membranaefaciens, Saccharomycodes ludwigii and Zygosaccharomyces bailii. Sensitivity to hydroxycinnamic acid was, in general, associated with sensitivity to potassium sorbate; at a given concentration potassium sorbate was more inhibitory than were any of the hydroxycinnamic acids.

The effect of hydroxycinnamic acids on the growth of wine‐spoilage lactic acid bacteria

Hydroxycinnamic acids and their derivatives occur naturally in grape juice and wine. To assess their potential as natural preservatives the effect of caffeic, coumaric and ferulic acids on the growth of three wine‐spoilage strains of Lactobacillus collinoides and one of Lact. brevis was studied in acid tomato broth containing 5% ethanol at pH 4.8. At concentrations of 500 and 1000 mg l‐1, all three compounds markedly inhibited growth; coumaric and ferulic acids were more effective than caffeic acid. At a concentration of 100 mg l‐1, all compounds stimulated growth. In general, the strains of Lact. collinoides were more susceptible both to inhibition and stimulation by the hydroxycinnamic acids than was the strain of Lact. brevis. The possible influence of hydroxycinnamic acids on the malolactic fermentation of wine is discussed.

Uncoupling Effect of Hydroxycinnamic Acid Derivatives on Pea Chloroplasts

Summary The effect of p-coumaric acids as well as the glucoside of caffeic acid at concentrations of 10-7 to 10-4 M on ferricyanide photoreduction, ATP synthesis and proton exchange parameters in pea chloroplasts has been studied. All the 3 compounds were shown to activate electron transport and to inhibit hotophosphorylation. Caffeic acid has the greatest effect, since it inhibits proton uptake by 40% at 10-4 M, whereas the dissipation constant of proton gradient has the greatest value under the effect of pcoumaric acid (140% at 10-4 M). The protolytic properties of the substances under study have been determined by the buffer capacity method. The ρssssK values of p-coumaric acid (4.8 and 9.15), caffeic acid (4.9; 8.85 and > 10) and caffeic acid glucoside (8.6 and > 10) were obtained. It is suggested that the uncoupling effect of hydroxycinnamic acids is due to their acid-base properties and the ability to form complexes with divalent metal ions.