Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties

The correlation between radical scavenging capacity and inhibitory activity in PhIP formation of 12 food-derived antioxidative phenolic compounds was investigated. Very poor correlation was found between their radical scavenging activity assessed by Trolox equivalent antioxidant capacity assay and PhIP formation inhibition in a model system. The effects of several of these polyphenols were further evaluated using beef patties. Remarkably, theaflavin 3,3'-digallate, epicatechin gallate, rosmarinic acid, and naringenin were capable of simultaneously reducing the levels of PhIP, MeIQx, and 4,8-DiMeIQx. Moreover, the inhibition of the formation of one of these HAs was not compromised by the inhibition of the formation of another HA. Naringenin, a flavonoid found in many citrus fruits, was found to be the most promising inhibitor in both chemical model system and beef patties, suggesting its great potential for practical application in daily cuisine.     

Four phenolic acids from purple sweet potato and their effects on physicochemical,digestive and structural characteristics of starch

Liquid chromatography coupled with tandem mass spectrometry (LC–MS/MS) was employed to investigate free phenols that were released from purple sweet potato (PSP) by alkaline, acid and enzymatic hydrolysis. Four phenolic acids, including ferulic, isoferulic, 4-hydroxybenzoic and caffeic acids, were identified. Based on their effects on the characteristics of purple sweet potato starch (PSPS), the four phenolic acids were studied. Furthermore, scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT–IR) and X-ray diffraction (XRD) techniques were employed to explore the microstructures of the complexes of the phenolic acids and PSPS. The obtained results demonstrated that the pasting, thermal, retrogradation, as well as digestive properties of PSPS were all influenced by the phenolic acids which interacted with PSPS through noncovalent hydrogen bonds. The influence of the four phenolic acids on the properties of PSPS was in the descending order: 4-hydroxybenzoic acid > ferulic acid > caffeic acid > isoferulic acid.     

Effects of phenolic acids and transglutaminase on soft wheat flour dough and baked products

BACKGROUND: The effects of phenolic acids on the physical properties of soft wheat flour dough and baked soft wheat flour products were investigated. Transglutaminase (TG) was added to observe the effects of non‐disulfide crosslinks on phenolic acid treated dough. Ferulic acid, p‐coumaric acid or fumaric acid was blended with pastry flour at a level of 250, 500 or 1000 ppm of flour dry weight, respectively. RESULTS: The addition of phenolic acids, TG or a mixture of phenolic acids and TG to flour had no effect on the mixing properties of the doughs but significantly affected 90 min rested dough. The addition of phenolic acids decreased the maximum resistance and increased the extensibility of 90 min rested dough, and TG reversed the effects of phenolic acids on the rested dough. The physical characteristics of cookies blended with each phenolic acid plus TG were not significantly different (P > 0.01) from those of the control cookies. However, TG with and without phenolic acids had significant effects on the moisture content, weight and volume of crackers. CONCLUSION: These results suggest that the addition of phenolic acids and TG in the absence of a fermentation process do not affect the physical properties of soft wheat flour products. The fermentation process allows the chemical reaction of the phenolic acids and TG to occur before the soft wheat flour products are baked. Copyright © 2008 Society of Chemical Industry     

Compositions of phenolic compounds,amino acids and reducing sugars in commercial potato varieties and their effects on acrylamide formation

BACKGROUND: Potato is consumed as an important source of carbohydrate and other nutrients as well as a good source of phenolics. Acrylamide is a potential carcinogen formed during frying of potato products. This study investigated the compositions of phenolic compounds, amino acids and reducing sugars in 16 commercial potato varieties from eight countries and analysed the relationships between these compositions and the levels of acrylamide generated by heating (185 °C, 25 min) potato powders. RESULTS: Major phenolic compounds in the tested potato varieties were identified as hydroxycinnamoylquinic/hydroxycinnamoyl derivatives by liquid chromatography/mass spectrometry. Great variations in the contents of phenolic compounds, free reducing sugars and amino acids as well as wide variations in acrylamide concentration were found among the different potato varieties. Correlation analysis revealed that fructose (r = 0.956***), glucose (r = 0.826***) and asparagine (r = 0.842***) were positively correlated with acrylamide formation. Interestingly, it was observed that higher levels of phenolic compounds were related to lower levels of acrylamide (r = ? 0.692*). CONCLUSION: Careful selection of potato varieties with lower levels of fructose, glucose and asparagine and higher levels of phenolic compounds may mitigate acrylamide formation during thermal processing of potato products. Copyright © 2010 Society of Chemical Industry     

Antioxidant activity versus cytotoxic and nuclear factor kappa B regulatory activities on HT-29 cells by natural fruit juices

The antioxidant activity (free radical scavenging ability and lipid oxidation inhibitory activity) and the activity in cell culture [influence on HT-29 human colon cancer cell viability and nuclear factor kappa B (NF-κB) activation] of natural fruit juices from red grape, strawberry, cherry and sour cherry were investigated in vitro. Analysis of polyphenolic composition of fruit juices showed the dominant presence of anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutinoside, peonidin-3-rutinoside, pelargonidin-3-glucoside), anthocyanidins (procyanidins B1, B2 and B3), flavonoids (glucosides of myricetin, quercetin and kaempferol), and phenolic acids (neochlorogenic acid, chlorogenic acid, ellagic acid, p-coumaroylquinic acid) in juices. DPPH test and β-carotene bleaching method indicated that grape, strawberry, cherry and sour cherry natural juices (at the concentration of 2.5%) showed very strong free radical scavenging (75–92%) and antioxidant activity (71–94%). In addition, at the concentration of 0.01% they showed complete inhibition of copper-induced oxidation of human LDL (low density lipoprotein). In contrast, selected fruit juices did not show cytotoxic effects on HT-29 cells and NF-κB inhibitory activity (at the concentrations of 0.5 and 2%). Results of this study showed no correlation between the antioxidant activity of natural fruit juices from red grape, strawberry, cherry and sour cherry and their effect on HT-29 cell viability and NF-κB inhibitory activity.     

Effect of phenolic acids on the rheological properties and proteins of hard wheat flour dough and bread

BACKGROUND: The effects of different phenolic acids on the rheological properties and gluten proteins of hard wheat flour dough and bread were investigated. Caffeic, ferulic, syringic and gallic acids were each blended with hard wheat flour at a concentration of 4.44 µmol L^?1 g^?1 flour. RESULTS: Mixing time and tolerance were reduced with the addition of phenolic acids. The phenolic acids reduced the maximum resistance to extension (R_max) and increased the extensibility of dough, with effects in the following order: gallic < syringic < ferulic < caffeic acid. The effect on R_max was more pronounced in overmixed dough. Loaf volume was most significantly decreased with the addition of caffeic acid. Extraction of sodium dodecyl sulfate‐soluble high‐molecular‐weight proteins was increased in both mixed and fermented doughs by the addition of ferulic and caffeic acids. The order of influence of the phenolic acids on the rheological properties and protein structure of dough and bread was consistent with that of their antioxidant activity. CONCLUSION: The addition of caffeic and ferulic acids reduced R_max and increased the extensibility of hard wheat flour dough by modifying the high‐molecular‐weight gluten, which resulted in decreased bread volume. Copyright © 2011 Society of Chemical Industry     

Effect of dietary soybean oil addition on the odd-numbered and branched-chain fatty acids in rabbit meat

The effect of dietary soybean oil (SO) inclusion (20 g/kg) on the odd-numbered (ONFA) and branched-chain (BCFA) fatty acids (FA) of two muscles, differing in fatness (Longissimus lumborum and Biceps femoris), was studied in 24 New Zealand × Californian rabbits. The increased muscle fatness in Biceps femoris (P < 0.001) was related to higher saturated (P < 0.01) and monounsaturated (P < 0.01) fatty acids. Intramuscular ONFA and BCFA contents were not affected, but their proportions were reduced (P < 0.01 and P < 0.001) by SO addition, suggesting a dilution effect of the dietary polyunsaturates accumulated in both muscles, except for 17:0i which decreased only in Longissimus lumborum due to significant (P < 0.05) soybean oil × muscle interaction. The higher (P < 0.05) BCFA contents and the FA profile in Biceps femoris were not affected by fatness, indicating an association with other muscle properties. The present study supplies new information on ONFA and BCFA in rabbit meat.     

Determination of free phenolic acids and antioxidant activity of methanolic extracts obtained from fruits and leaves of Chenopodium album

In this study, determination of phenolic acids as well as investigation of antioxidant activity of methanolic extracts from the fruits and leaves of Chenopodium album is described. Extracts were subjected to acidic hydrolysis in order to obtain total free phenolic acids. However, some of phenolic acids were identified and quantified by HPLC-DAD. The results were confirmed by LC-MS equipped with MS-ESI. In addition, Folin–Ciocalteu method was applied to determine the total phenolic contents. The antioxidant activity of C. album extracts was examined by using DPPH and hydroxyl radical-scavenging activity assays. Results revealed that the leaves extract exhibits better performance in antioxidant assays and in the higher total phenolic contents (3066 mg of GAE/100 g) when compared to fruits extract (1385 mg of GAE/100 g). From these results it has been revealed that the methanolic extracts of C. album from fruits and leaves have great potential as a source for natural health products.     

Effect of commercial or depurinized milk on rat liver growth-regulatory kinases,nuclear factor-kappa B,and endonuclease in experimental hyperuricemia: Comparison with allopurinol therapy

Hyperuricemia is a biochemical hallmark of gout, renal urate lithiasis, and inherited purine disorders, and may be a result of enormous ATP breakdown or purine release as a result of cardiovascular disease, hypertension, kidney disease, eclampsia, obesity, metabolic syndrome, psoriasis, tumor lysis syndrome, or intense physical training. The beneficial role of dairy products on hyperuricemia management and prevention is well documented in the literature. The primary aim of our experimental study was to examine the effect of milk dietary regimen (commercial 1.5% fat UHT milk or patented depurinized milk) compared with allopurinol therapy on experimental hyperuricemia induced by oxonic acid in rats. Principal component analysis was applied on a data set consisting of 11 variables for 8 different experimental groups. Among the 11 parameters measured (plasma uric acid and the liver parameters NFκB-p65, Akt kinase/phospho-Akt kinase, ERK kinase/phospho-ERK kinase, IRAK kinase/phospho IRAK kinase, p38/phospho-p38, and DNase), Akt/phospho Akt and ERK/phospho-ERK signaling were extracted as the most discriminating. We also compared the content of various potentially toxic compounds (sulfur compounds, ketones, aldehydes, alcohols, esters, carboxylic acids, and phthalates) in untreated commercial milk and depurinized milk. Of all the compounds investigated in this study that were observed in commercial milk (24 volatile organic compounds and 4 phthalates), 6 volatile organic compounds were not detected in depurinized milk. For almost all of the other compounds, significant decreases in concentration were observed in depurinized milk compared with commercial milk. In conclusion, a depurinized milk diet may be recommended in nutritional treatment of primary and secondary hyperuricemia to avoid uric acid and other volatile, potentially toxic compounds that may slow down liver regeneration and may induce chronic liver diseases.     

Cytoprotective and antioxidant activity of free,conjugated and insoluble-bound phenolic acids from swallow root (Decalepis hamiltonii)

Swallow root (Decalepis hamiltonii) was extracted for free (SRFP), conjugated (SRCP) and insoluble-bound phenolic acids (SRIBP), and evaluated for cytoprotectivity, 1,1,diphenyl-2-picrylhydrazyl (DPPH) scavenging ability, reducing power and protection to DNA damage. In addition, the constituent phenolic acids in the extracts were also analysed. Results indicated a total phenol content of 20.72, 7.97 and 11.52 mg gallic acid equivalents (GAE)/g for SRFP, SRCP and SRIBP extracts, respectively. At 0.12 μg/mL concentration SRCP showed 87% cytoprotection (on NIH 3T3 cells) compared to SRFP (47%) and SRIBP (65%). DPPH radical scavenging activity indicated an IC₅₀ of 0.046, 0.06 and 0.128 μg/mL for SRCP, SRIBP and SRFP, respectively. Also, SRCP showed higher reducing power and DNA protectivity (80%). HPLC analysis of phenolic acid extracts showed the presence of hydroxybenzoate and cinnamate derivatives. Among the phenolics identified gallic, gentisic, protocatechuic and p-coumaric acids were the major contributors to antioxidant activity.     

Antioxidant activity and antimicrobial properties of phenolic extracts from acerola (Malpighia emarginata DC) fruit

The antioxidant activity and antimicrobial property of phenolic extracts from acerola (Malpighia emarginata DC) fruit were assessed. The contribution of ascorbic acid and phenolic compounds in the total antioxidant capacity of the extracts was also evaluated. The extracts showed high total phenolic values and possessed high antioxidant activity as expressed by 2,2′‐diphenylpicrylhydrazyl (DPPH) and oxygen radical absorbance capacity assays (ORAC). The ascorbic acid content ranged from 405 to 1744 mg/100 g of fruit on a fresh weight basis. The antioxidant capacity of the phenolic fractions was in the following order: anthocyanins<phenolic acids<flavonoids. The phenolic fractions contributed 7.1–36.5% of the antioxidant activity expressed by ORAC, whereas the contribution of ascorbic accounted for 18–39% of the total activity. Selected extracts from the flavonoids fraction showed some activity against Staphylococcus aureus.     

Free fatty acids impair autophagic activity and activate nuclear factor kappa B signaling and NLR family pyrin domain containing 3 inflammasome in calf hepatocytes

Free fatty acids (FFA)-induced hepatic inflammation agravates liver injury and metabolic dysfunction in dairy cows with ketosis or fatty liver. Under stressful conditions, autophagy is generally considered as a cell protection mechanism, but whether the FFA-induced inflammatory and stress effect on hepatocytes involves an autophagy response is not well known. Thus, the objective of this study was to investigate the effects of FFA on autophagy and the role of autophagy in the activation of NF-κB (nuclear factor kappa B) signaling and NLRP3 (NLR family pyrin domain containing 3) inflammasome in calf hepatocytes. Calf hepatocytes were isolated from 3 healthy Holstein female new-born calves (1 d of age, 30–40 kg) and exposed to various concentrations of FFA (0, 0.3, 0.6, or 1.2 mM) after treatment with or without the autophagy inhibitor chloroquine (CQ) or the autophagy activator rapamycin. Expression of autophagy markers, LC3 (microtubule-associated protein 1 light chain 3) and p62 (sequestosome 1), NF-κB signaling, and NLRP3 inflammasome-related molecules were analyzed via western blot and quantitative real-time PCR. Results revealed that 0.6 and 1.2 mM FFA activated NF-κB signaling and NLRP3 inflammasome as indicated by an elevated ratio of p-NF-κB/NF-κB, protein abundance of NLRP3 and CASP1 (caspase 1), activity of CASP1, and mRNA abundance of IL1B and IL18. In addition, hepatocyte treated with 0.6 and 1.2 mM FFA or autophagy inhibitor CQ displayed increased protein abundance of p62 and LC3-II. Moreover, there was no difference in protein abundance of p62 and LC3-II between calf hepatocytes treated with 1.2 mM FFA and 1.2 mM FFA plus CQ, indicating that FFA inhibits autophagic activity in calf hepatocytes. Treatment with CQ led to overactivation of NF-κB signaling and NLRP3 inflammasome. Furthermore, CQ plus 1.2 mM FFA aggravated FFA-induced inflammation. In contrast, induction of autophagy by rapamycin ameliorated the FFA-activated NF-κB signaling and NLRP3 inflammasome as demonstrated by a lower ratio of p-NF-κB/NF-κB, protein abundance of NLRP3 and CASP1, activity of CASP1, and mRNA abundance of IL1B and IL18. Overall, inhibition of autophagy exacerbated, whereas induction of autophagy alleviated, FFA-induced inflammatory processes in calf hepatocytes, suggesting that impairment of autophagy might be partly responsible for hepatic inflammation and subsequent liver injury in dairy cows with ketosis or fatty liver. As such, regulation of autophagy may be an effective therapeutic strategy for controlling overt inflammatory responses in vivo.     

The effects of solvents on the phenolic contents and antioxidant activity of Stypocaulon scoparium algae extracts

Water, water/methanol (1/1), methanol and ethanol crude extracts from a brown alga Stypocaulon scoparium were examined for total phenolic contents (TPC) using Folin–Ciocalteu method. DPPH scavenging assay was performed to measure the radical scavenging activities (RSA) of the extracts. Results showed a significant association between the antioxidant potency and the TPC. The aqueous extract showed both, the highest antioxidant activity and highest phenolic contents. The identification and quantification of phenolic antioxidants were carried out with a rapid and simple method of reverse phase high performance liquid chromatography (RP-HPLC). This method was developed for the simultaneous analysis of 14 polyphenols, namely gallic acid, catechin, epicatechin, rutin, p-coumaric acid, myricetin, quercetin and protocatechuic, vanillic, caffeic, ferulic, chlorogenic, syringic and gentisic acids. The chromatographic separation of 14 polyphenols was achieved in less than 40 min by RP-HPLC (Varian, Pursuit XRs C18 column, 5 μm, 250 mm × 4.6 mm) using linear gradient elution of methanol and water (0.1% formic acid) with a flow rate of 1 ml/min. Gallic acid was by far the predominant polyphenol.     

Sugars,organic acids,phenolic composition and antioxidant activity of sweet cherry (Prunus avium L.)

Sugars, organic acids, phenolics and anthocyanins in fruits of 13 sweet cherry cultivars: Badascony, Burlat, Early Van Compact, Fercer, Fernier, Ferprime, Lala Star, Lapins, Noire de Meched, Sylvia, Vesseaux, Vigred (red-coloured) and Ferrador (bi-coloured) were quantified by HPLC. Sweet cherry cultivars of different pomological characteristics and different time of ripening were evaluated sensorily. Cultivars were evaluated for their total phenolic content and antioxidant activity. The sum of sugars (glucose, fructose, sucrose and sorbitol) ranged from 125 to 265 g/kg fresh weight (FW) and the sum of organic acids (malic, citric, shikimic and fumaric) ranged from 3.67 to 8.66 g/kg FW. Total phenolic content ranged from 44.3 to 87.9 mg gallic acid equivalents/100 g FW and antioxidant activity ranged from 8.0 to 17.2 mg ascorbic acid equivalent antioxidant capacity mg/100 g FW. The correlation of antioxidant activity with total phenolics content and content of anthocyanins was cultivar dependent.     

Influence of dietary phenolic acids on redox status of iron: Ferrous iron autoxidation and ferric iron reduction

We investigated the effect of dietary phenolic acids on the oxidation of Fe²⁺ caused by molecular oxygen. All phenolic acids bearing 3,4-dihydroxy (catechol) or 3,4,5-trihydroxy (galloyl) moiety formed chelates with ferric iron and significantly increased the rate of Fe²⁺ autoxidation. The carboxylate group and catechol substitution instead of galloyl moiety facilitated the ferrous ion oxidation more effectively. Caffeic acid and protocatechuic acid, the strongest accelerators of Fe²⁺ autoxidation, were able to facilitate autoxidation at concentrations lower than 1% of the initial amount of Fe²⁺. Therefore chelates of these catecholic acids with iron displayed ferroxidase-like activity. Conversely, when we started from ferric ions, catechols partially formed ferrous ions in the presence of ferrozine. Thus, catecholic acids formed stable chelates with iron, in which ferric ion is the dominant species, but the redox cycling of iron between Fe²⁺ and Fe³⁺ in chelates probably plays a crucial role in the catalysis of ferrous iron autoxidation. Interestingly, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid and vanillic (4-hydroxy-3-methoxybenzoic) acid protected ferrous ions from autoxidation as effectively as ascorbic acid and cysteine. These monophenolic acids, differently from ascorbic acid and cysteine, were not able to reduce ferric ions. Syringic (3,5-dimethoxy-4-hydroxybenzoic) acid did not alter the redox state of iron, only in a large excess over metal, syringic acid slightly inhibited ferrous ions autoxidation and partially reduced ferric ions. Therefore, the effects of syringic acid at high concentration were similar but much lower to those of ascorbic acid and cysteine. The biological importance of ferroxidase-like activity of polyphenols, especially the influence on iron absorption, is also discussed.     

Phenolic acid content and radical scavenging activity of extracts from medlar (Mespilus germanica L.) fruit at different stages of ripening

The medlar fruit (Mespilus germanica L.) has been gaining commercial importance in recent years, attracting research on its chemical composition. In this study, we have investigated how the degree of ripeness affects the concentrations and proportions of phenolic acids. The DPPH scavenging activity and the total phenolic content (TPC) were determined. Five stages of fruit maturity were studied and eight phenolic acids (protocatechuic, 4-hydroxybenzoic, syringic, 3-hydroxybenzoic, caffeic, salicylic, 4-coumaric and sinapic) were determined by HPLC–MS. The concentrations of phenolic acids mostly decreased as the fruit ripening progressed, except for insoluble ester-bound phenolics, which increased at the early stages of maturity and decreased only during the ripe to over-ripe stage of maturity. The DPPH scavenging activity also decreased during fruit maturation, suggesting a decrease of natural antioxidants in fruit. A strong correlation between TPC and antioxidant capacity measured by the DPPH method was found. The data presented demonstrates the influence of ripening on the phenolic acid content and antioxidant properties of medlar fruit.