Hypochlorous acid-activated carbon: an oxidizing agent capable of producing hydroxylated polychlorinated biphenyls.

PubMed Central

Voudrias, E A; Larson, R A; Snoeyink, V L; Chen, A S; Stapleton, P L

1986-01-01

Granular activated carbon (GAC), in the presence of dilute aqueous hypochlorite solutions typical of those used in water treatment, was converted to a reagent capable of carrying out free-radical coupling reactions and other oxidations of dilute aqueous solutions of phenols. The products included biphenyls with chlorine and hydroxyl substitution (hydroxylated polychlorinated biphenyls). For example, 2,4-dichlorophenol, a common constituent of wastewaters and also natural waters treated with hypochlorite, was converted to 3,5,5'trichloro-2,4'-dihydroxybiphenyl and several related compounds in significant amounts. It is possible that these products pose more of a health hazard than either the starting phenols or the unhydroxylated polychlorinated biphenyl derivatives. PMID:3028770

Carbonic Anhydrase and Urease Inhibitory Potential of Various Plant Phenolics Using in vitro and in silico Methods.

PubMed

Rauf, Abdur; Raza, Muslim; Saleem, Muhammad; Ozgen, Ufuk; Karaoglan, Esen Sezen; Renda, Gulin; Palaska, Erhan; Orhan, Ilkay Erdogan

2017-06-01

Plant phenolics are known to display many pharmacological activities. In the current study, eight phenolic compounds, e.g., luteolin 5-O-β-glucoside (1), methyl rosmarinate (2), apigenin (3), vicenin 2 (4), lithospermic acid (5), soyasaponin II (6), rubiadin 3-O-β-primeveroside (7), and 4-(β-d-glucopyranosyloxy)benzyl 3,4-dihydroxybenzoate (8), isolated from various plant species were tested at 0.2 mm against carbonic anhydrase-II (CA-II) and urease using microtiter assays. Urease inhibition rate for compounds 1 - 8 ranged between 5.0 - 41.7%, while only compounds 1, 2, and 4 showed a considerable inhibition over 50% against CA-II with the IC 50 values of 73.5 ± 1.05, 39.5 ± 1.14, and 104.5 ± 2.50 μm, respectively, where IC 50 of the reference (acetazolamide) was 21.0 ± 0.12 μm. In silico experiments were also performed through two docking softwares (Autodock Vina and i-GEMDOCK) in order to find out interactions between the compounds and CA-II. Actually, compounds 6 (30.0%) and 7 (42.0%) possessed a better binding capability toward the active site of CA-II. According to our results obtained in this study, among the phenolic compounds screened, particularly 1, 2, and 4 appear to be the promising inhibitors of CA-II and may be further investigated as possible leads for diuretic, anti-glaucoma, and antiepileptic agents. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Antifungal and Antiochratoxigenic Activities of Essential Oils and Total Phenolic Extracts: A Comparative Study

PubMed Central

EL Khoury, Rachelle; Atoui, Ali; Mathieu, Florence; Kawtharani, Hiba; EL Khoury, Anthony; Maroun, Richard G.; EL Khoury, Andre

2017-01-01

This study is intended to prevent ochratoxin A (OTA) production by Aspergillus carbonarius S402 using essential oils (EOs) and total phenolic compounds extracted from plants and herbs. The EOs used in this study are the following: bay leaves, cumin, fenugreek, melissa, mint, and sage. As for the phenolic compounds, they were extracted from bay leaves, cumin, fenugreek, melissa, mint, sage, anise, chamomile, fennel, rosemary, and thyme. The experiments were conducted on Synthetic Grape Medium (SGM) medium at 28 °C for 4 days. OTA was extracted from the medium with methanol and quantified using HPLC (High Performance Liquid Chromatography). Results showed that EOs had a greater impact than the total phenolic extracts on the OTA production. Reduction levels ranged between 25% (sage) and 80% (melissa) for the EOs at 5 µL mL−1, and 13% (thyme) and 69% (mint) for the phenolic extracts. Although they did not affect the growth of A. carbonarius, total phenolic extracts and EOs were capable of partially reducing OTA production. Reduction levels depended on the nature of the plants and the concentration of the EOs. Reducing OTA with natural extracts could be a solution to prevent OTA production without altering the fungal growth, thus preserving the natural microbial balance. PMID:28698493

The influence of interactions among phenolic compounds on the antiradical activity of chokeberries (Aronia melanocarpa).

PubMed

Jakobek, Lidija; Seruga, Marijan; Krivak, Petra

2011-06-01

In the present work, interactions between phenolic compounds from chokeberries and their influence on the antiradical activity was studied. Three fractions were isolated from chokeberries containing different classes of phenolic compounds. The first fraction contained a major part of phenolic acids and flavonols, the second anthocyanins, and the third insoluble phenols and proanthocyanidins. The phenolic compound content was determined using high-performance liquid chromatography, and the antiradical activity using the DPPH test. In order to evaluate the effects of interactions between phenolic compounds on the antiradical activity, the antiradical activity of individual phenolic fractions was compared with that obtained by mixing phenolic fractions. Phenolic mixtures showed the decrease in the antiradical activity in comparison with the individual phenolic fractions. These results suggest the existence of complex interactions among phenolic compounds that caused the decrease of the antiradical activity. Interactions among chokeberry phenols promoted a negative synergism.

Investigation of chitosan-phenolics systems as wood adhesives.

PubMed

Peshkova, Svetlana; Li, Kaichang

2003-04-24

Chitosan-phenolics systems were investigated as wood adhesives. Adhesion between two pieces of wood veneer developed only when all three components-chitosan, a phenolic compound, and laccase-were present. For the adhesive systems containing a phenolic compound with only one phenolic hydroxyl group, adhesive strengths were highly dependent upon the chemical structures of phenolic compounds used in the system and the relative oxidation rates of the phenolic compounds by laccase. The adhesive strengths were also directly related to the viscosity of the adhesive systems. However, for the adhesive systems containing a phenolic compound with two or three phenolic hydroxyl groups adjacent to each other, no correlations among adhesive strengths, relative oxidation rates of the phenolic compounds by laccase, and viscosities were observed. The adhesion mechanisms of these chitosan-phenolics systems were proposed to be similar to those of mussel adhesive proteins.

Phenolic composition and antioxidant potential of grain legume seeds: A review.

PubMed

Singh, Balwinder; Singh, Jatinder Pal; Kaur, Amritpal; Singh, Narpinder

2017-11-01

Legumes are a good source of bioactive phenolic compounds which play significant roles in many physiological as well as metabolic processes. Phenolic acids, flavonoids and condensed tannins are the primary phenolic compounds that are present in legume seeds. Majority of the phenolic compounds are present in the legume seed coats. The seed coat of legume seeds primarily contains phenolic acids and flavonoids (mainly catechins and procyanidins). Gallic and protocatechuic acids are common in kidney bean and mung bean. Catechins and procyanidins represent almost 70% of total phenolic compounds in lentils and cranberry beans (seed coat). The antioxidant activity of phenolic compounds is in direct relation with their chemical structures such as number as well as position of the hydroxyl groups. Processing mostly leads to the reduction of phenolic compounds in legumes owing to chemical rearrangements. Phenolic content also decreases due to leaching of water-soluble phenolic compounds into the cooking water. The health benefits of phenolic compounds include acting as anticarcinogenic, anti-thrombotic, anti-ulcer, anti-artherogenic, anti-allergenic, anti-inflammatory, antioxidant, immunemodulating, anti-microbial, cardioprotective and analgesic agents. This review provides comprehensive information of phenolic compounds identified in grain legume seeds along with discussing their antioxidant and health promoting activities. Copyright © 2017 Elsevier Ltd. All rights reserved.

Distribution and potential ecological risk of 50 phenolic compounds in three rivers in Tianjin, China.

PubMed

Zhong, Wenjue; Wang, Donghong; Wang, Zijian

2018-04-01

Phenolic compounds widely exist in the surface water of many countries; however, few studies have simultaneously analyzed and evaluated broad-spectrum phenolic compounds in various components of the water environment. Therefore this study analyzed the distribution and potential ecological risk of 50 phenolic compounds in the surface water, sediment and suspended particulate matter of three important rivers in Tianjin, the main heavy industry city with high pollution in China. The qualitative results show that phenolic pollution existed extensively in the three rivers and the kinds of phenolic compounds in the water were relatively higher than in both sediment and suspended particulate matter. The quantitative results show that the phenolic pollution in the wet-season samples was serious than dry-season samples. Meanwhile, total concentrations of phenolic compounds in three components from the Dagu Drainage River (DDR) were all much higher than those in the Beitang Drainage River (BDR) and Yongdingxin River (YDXR). The highest total concentrations of phenolic compounds in three components all appeared in wet-season samples in DDR, and the highest total concentration was 1354 μg/L in surface water, 719 μg/kg dw in suspended particulate matter and 2937 μg/kg dw in sediment, respectively. The ecological risk of phenolic compounds in surface water was evaluated using the quotient method, and phenolic compounds with risk quotient (RQ) > 1 (RQ > 0.3 for YDXR) were identified as priority pollutants. Five kinds of phenolic compounds were identified as priority phenolic compounds in BDR, and the order of risk was 2-cresol > 2,4-xylenol > 2-sec-butylphenol > 2-naphthol > 3-cresol. Six kinds of phenolic compounds were identified as priority phenolic compounds in DDR, and the order of risk was 2-naphthol > p-chloro-m-xylenol > 4-cresol > 3-cresol > 2,4-xylenol > 2,3,6-Trimethylphenol. In YDXR, only phenol, 2-naphthol and 2,4-xylenol were identified as priority phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Influence of Various Phenolic Compounds on Properties of Gelatin Film Prepared from Horse Mackerel Trachurus japonicus Scales.

PubMed

Le, Thuy; Maki, Hiroki; Okazaki, Emiko; Osako, Kazufumi; Takahashi, Kigen

2018-06-15

Influence of various phenolic compounds on physical properties and antioxidant activity of gelatin film from horse mackerel Trachurus japonicus scales was investigated. Tensile strength (TS) of the film was enhanced whereas elongation at break was declined by adding 1% to 5% phenolic compounds. Rutin was the most effective to improve the TS compared to the other tested phenolic compounds including ferulic acid, caffeic acid, gallic acid, and catechin. Gelatin films with the phenolic compounds showed the excellent UV barrier properties. FTIR spectra exhibited that wavenumber of amide-A band of films decreased with formation of hydrogen bonding between amino groups of gelatin and hydroxyl groups of the phenolic compounds. Gelatin film incorporated with rutin which has the largest number of hydroxyl groups among the tested compounds demonstrated the lowest wavenumber for the amide-A peak. It is indicated that hydroxyl groups contained in the phenolic compounds contribute to formation of hydrogen bonds involved in improvement of the mechanical properties of the films. The incorporation of the phenolic compounds with gelatin films also led to the increasing of total phenolic contents and DPPH radical scavenging activities. Thus, it is concluded that phenolic compounds can promote the quality of gelatin film. Properties of gelatin film derived from horse mackerel scales can be improved by adding of phenolic compounds. Phenolic compounds containing a large number of hydroxyl groups should be selected to enhance physical properties of the gelatin film. A biodegradable film prepared from horse mackerel gelatin incorporated with phenolic compounds, which has good physical properties and antioxidant properties, can solve environmental problems caused by synthetic plastic materials. © 2018 Institute of Food Technologists®.

Degradation and induction specificity in actinomycetes that degrade p-nitrophenol.

PubMed Central

Hanne, L F; Kirk, L L; Appel, S M; Narayan, A D; Bains, K K

1993-01-01

We have isolated two soil bacteria (identified as Arthrobacter aurescens TW17 and Nocardia sp. strain TW2) capable of degrading p-nitrophenol (PNP) and numerous other phenolic compounds. A. aurescens TW17 contains a large plasmid which correlated with the PNP degradation phenotype. Degradation of PNP by A. aurescens TW17 was induced by preexposure to PNP, 4-nitrocatechol, 3-methyl-4-nitrophenol, or m-nitrophenol, whereas PNP degradation by Nocardia sp. strain TW2 was induced by PNP, 4-nitrocatechol, phenol, p-cresol, or m-nitrophenol. A. aurescens TW17 initially degraded PNP to hydroquinone and nitrite. Nocardia sp. strain TW2 initially converted PNP to hydroquinone or 4-nitrocatechol, depending upon the inducing compound. PMID:8250573

Phenol and chlorinated phenols exhibit different apoptotic potential in human red blood cells (in vitro study).

PubMed

Michałowicz, Jaromir; Włuka, Anna; Cyrkler, Monika; Maćczak, Aneta; Sicińska, Paulina; Mokra, Katarzyna

2018-05-23

Phenol and chlorinated phenols are widely spread in the environment and human surrounding, which leads to a common environmental and occupational exposure of humans to these substances. The aim of this study was to assess eryptotic changes in human red blood cells treated with phenol, 2,4-dichlorophenol (2,4-DCP), 2,4,6-trichlorophenol (2,4,6-TCP) and pentachlorophenol (PCP). The erythrocytes were incubated with phenols studied in the concentrations ranging from 1 to 100 μg/mL for 24 h or 48 h. The results of the study revealed that all compounds studied caused phosphatidylserine translocation and increased cytosolic calcium ions level in human erythrocytes. It was also noticed that phenol and chlorophenols caused an increase in caspase-3 and calpain activation, which confirmed that they were capable of inducing suicidal death of erythrocytes. The results also revealed that PCP most strongly altered the parameters studied, while phenol exhibited the weakest eryptotic potential in the incubated cells. Copyright © 2018 Elsevier B.V. All rights reserved.

EMERGING TECHNOLOGY BULLETIN: REMOVAL OF PHENOL FROM AQUEOUS SOLUTIONS USING HIGH ENERGY ELECTRON BEAM IRRADIATION

EPA Science Inventory

Irradiation of aqueous solutions with high-energy electrons results in the formation of the aqueous electron, hydrogen radical, H-, and the hydroxyl radical, OH-. These reactive transient species initiate chemical reactions capable of destroying organic compounds in aqueous solut...

Pulse seed germination improves antioxidative activity of phenolic compounds in stripped soybean oil-in-water emulsions.

PubMed

Xu, Minwei; Jin, Zhao; Peckrul, Allen; Chen, Bingcan

2018-06-01

The purpose of this study was to investigate antioxidative activity of phenolic compounds extracted from germinated pulse seed including chickpeas, lentils and yellow peas. Phenolic compounds were extracted at different germination time and total phenolic content was examined by Folin Ciocalteu's reaction. Antioxidative activity of extracts was characterized by in vitro assay including 2, 2-diphenyl-1-picrylhydrazyl radical scavenging capacity (DPPH), oxygen radical absorbance capacity (ORAC), iron-binding assay, and in stripped soybean oil-in-water emulsions. The results suggested that germination time is critical for phenolic compounds production. The form variation of phenolic compounds influenced the antioxidative activity of phenolic compounds both in vitro assay and in emulsion systems. Soluble bound phenolic compounds showed higher antioxidative ability in emulsion system with the order of chickpea > yellow pea > lentil. On the basis of these results, soluble bound phenolic compounds may be considered as a promising natural antioxidant to prevent lipid oxidation in foods. Copyright © 2018 Elsevier Ltd. All rights reserved.

Comprehensive Characterization of Extractable and Nonextractable Phenolic Compounds by High-Performance Liquid Chromatography-Electrospray Ionization-Quadrupole Time-of-Flight of a Grape/Pomegranate Pomace Dietary Supplement.

PubMed

Pérez-Ramírez, Iza F; Reynoso-Camacho, Rosalía; Saura-Calixto, Fulgencio; Pérez-Jiménez, Jara

2018-01-24

Grape and pomegranate are rich sources of phenolic compounds, and their derived products could be used as ingredients for the development of functional foods and dietary supplements. However, the profile of nonextractable or macromolecular phenolic compounds in these samples has not been evaluated. Here, we show a comprehensive characterization of extractable and nonextractable phenolic compounds of a grape/pomegranate pomace dietary supplement using high-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight (HPLC-ESI-QTOF) and matrix-assisted laser desorption/ionization (MALDI)-TOF techniques. The main extractable phenolic compounds were several anthocyanins (principally malvidin 3-O-glucoside) as well as gallotannins and gallagyl derivatives; some phenolic compounds were reported in grape or pomegranate for the first time. Additionally, there was a high proportion of nonextractable phenolic compounds, including vanillic acid, and dihydroxybenzoic acid. Unidentified polymeric structures were detected by MALDI-TOF MS analysis. This study shows that mixed grape and pomegranate pomaces are a source of different classes of phenolic compounds including a high proportion of nonextractable phenolic compounds.

Using minced horseradish roots and peroxides for the deodorization of swine manure: a pilot scale study.

PubMed

Govere, Ephraim M; Tonegawa, Masami; Bruns, Mary Ann; Wheeler, Eileen F; Kephart, Kenneth B; Voigt, Jean W; Dec, Jerzy

2007-04-01

Enzymes that have proven to be capable of removing toxic compounds from water and soil may also be useful in the deodorization of animal manures. Considering that pork production in the US is a $40-billion industry with over half a million workers, odor control to protect air quality in the neighboring communities must be considered an essential part of managing livestock facilities. This pilot scale (20-120 L) study tested the use of minced horseradish (Armoracia rusticana L.) roots (1:10 roots to swine slurry ratio), with calcium peroxide (CaO(2) at 34 mM) or hydrogen peroxide (H(2)O(2) at 68 mM), to deodorize swine slurry taken from a 40,000-gallon storage pit at the Pennsylvania State University's Swine Center. Horseradish is known to contain large amounts of peroxidase, an enzyme that, in the presence of peroxides, can polymerize phenolic odorants and thus reduce the malodor. Twelve compounds commonly associated with malodor (seven volatile fatty acids or VFAs, three phenolic compounds and two indolic compounds) were used as odor indicators. Their concentration in swine slurry before and after treatment was determined by gas chromatography (GC) to assess the deodorization effect. The pilot scale testing demonstrated a complete removal of phenolic odorants (with a detection limit of 0.5 mg L(-1)) from the swine slurry, which was consistent with our previous laboratory experiments using 30-mL swine slurry samples. Horseradish could be recycled (reused) five times while retaining significant reduction in the concentration of phenolic odorants. In view of these findings, inexpensive plant materials, such as horseradish, represent a promising tool for eliminating phenolic odorants from swine slurry.

Fast separation and determination of tyrosol, hydroxytyrosol and other phenolic compounds in extra-virgin olive oil by capillary zone electrophoresis with ultraviolet-diode array detection.

PubMed

Bonoli, Matteo; Montanucci, Marina; Gallina Toschi, Tullia; Lercker, Giovanni

2003-09-05

Olive oil is the main source of fat in the Mediterranean diet, and its consumption has been related to a low incidence of coronary heart disease and certain cancers. Recent findings demonstrate that olive oil phenolics are powerful in vitro and in vivo antioxidants and display other biological activities that could partially account for the observed healthful effects of the Mediterranean diet. A detailed method optimization plan was carried out to separate the most popular phenols in olive oil for four separation parameters: buffer concentration, buffer pH, applied voltage and temperature. Consequently, an analytical method capable of separating 21 different phenols and polyphenols by capillary zone electrophoresis was developed; the separation was performed within 10 min, using a 40 cm x 50 microm capillary, with a 45 mM sodium tetraborate buffer (pH 9.60), at 27 kV and 30 degrees C. The optimized method was applied to methanolic extracts of several Italian extra-virgin olive oils obtained by different technologies in order to characterize and to compare their antioxidant profile. Positive correlations of phenolic compounds found by capillary zone electrophoresis (CZE) and two colorimetric indexes (total polyphenols and o-diphenols) were found and discussed.

LC-MS analysis of phenolic compounds and antioxidant activity of buckwheat at different stages of malting.

PubMed

Terpinc, Petra; Cigić, Blaž; Polak, Tomaž; Hribar, Janez; Požrl, Tomaž

2016-11-01

The impact of malting on the profile of the phenolic compounds and the antioxidant properties of two buckwheat varieties was investigated. The highest relative increases in phenolic compounds were observed for isoorientin, orientin, and isovitexin, which are consequently major inducible phenolic compounds during malting. Only a minor relative increase was observed for the most abundant phenolic compound, rutin. The radical-scavenging activity of buckwheat seeds was evaluated using ABTS and DPPH assays. A considerable increase in total phenolic compounds and higher antioxidant activity were observed after 64h of germination, whereas kilning resulted in decreased total phenolic compounds and antioxidant activity. Higher antioxidant activities for extracts were found for buffered solvents than for pure methanol and water. Changes in the composition of the phenolic compounds and increased antioxidant content were confirmed by several methods, indicating that buckwheat malt can be used as a food rich in antioxidants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Analysis of phenolic compounds in different parts of pomegranate (Punica granatum) fruit by HPLC-PDA-ESI/MS and evaluation of their antioxidant activity: application to different Italian varieties.

PubMed

Russo, Marina; Fanali, Chiara; Tripodo, Giusy; Dugo, Paola; Muleo, Rosario; Dugo, Laura; De Gara, Laura; Mondello, Luigi

2018-06-01

The analysis of pomegranate phenolic compounds belonging to different classes in different fruit parts was performed by high-performance liquid chromatography coupled with photodiode array and mass spectrometry detection. Two different separation methods were optimized for the analysis of anthocyanins and hydrolyzable tannins along with phenolic acids and flavonoids. Two C 18 columns, core-shell and fully porous particle stationary phases, were used. The parameters for separation of phenolic compounds were optimized considering chromatographic resolution and analysis time. Thirty-five phenolic compounds were found, and 28 of them were tentatively identified as belonging to four different phenolic compound classes; namely, anthocyanins, phenolic acids, hydrolyzable tannins, and flavonoids. Quantitative analysis was performed with a mixture of nine phenolic compounds belonging to phenolic compound classes representative of pomegranate. The method was then fully validated in terms of retention time precision, expressed as the relative standard deviation, limit of detection, limit of quantification, and linearity range. Phenolic compounds were analyzed directly in pomegranate juice, and after solvent extraction with a mixture of water and methanol with a small percentage of acid in peel and pulp samples. The accuracy of the extraction method was also assessed, and satisfactory values were obtained. Finally, the method was used to study identified analytes in pomegranate juice, peel, and pulp of six different Italian varieties and one international variety. Differences in phenolic compound profiles among the different pomegranate parts were observed. Pomegranate peel samples showed a high concentration of phenolic compounds, ellagitannins being the most abundant ones, with respect to pulp and juice samples for each variety. With the same samples, total phenols and antioxidant activity were evaluated through colorimetric assays, and the results were correlated among them.

Synergistic anti-Campylobacter jejuni activity of fluoroquinolone and macrolide antibiotics with phenolic compounds

PubMed Central

Oh, Euna; Jeon, Byeonghwa

2015-01-01

The increasing resistance of Campylobacter to clinically important antibiotics, such as fluoroquinolones and macrolides, is a serious public health problem. The objective of this study is to investigate synergistic anti-Campylobacter jejuni activity of fluoroquinolones and macrolides in combination with phenolic compounds. Synergistic antimicrobial activity was measured by performing a checkerboard assay with ciprofloxacin and erythromycin in the presence of 21 phenolic compounds. Membrane permeability changes in C. jejuni by phenolic compounds were determined by measuring the level of intracellular uptake of 1-N-phenylnaphthylamine (NPN). Antibiotic accumulation assays were performed to evaluate the level of ciprofloxacin accumulation in C. jejuni. Six phenolic compounds, including p-coumaric acid, sinapic acid, caffeic acid, vanillic acid, gallic acid, and taxifolin, significantly increased the susceptibility to ciprofloxacin and erythromycin in several human and poultry isolates. The synergistic antimicrobial effect was also observed in ciprofloxacin- and erythromycin-resistant C. jejuni strains. The phenolic compounds also substantially increased membrane permeability and antibiotic accumulation in C. jejuni. Interestingly, some phenolic compounds, such as gallic acid and taxifolin, significantly reduced the expression of the CmeABC multidrug efflux pump. Phenolic compounds increased the NPN accumulation in the cmeB mutant, indicating phenolic compounds may affect the membrane permeability. In this study, we successfully demonstrated that combinational treatment of C. jejuni with antibiotics and phenolic compounds synergistically inhibits C. jejuni by impacting both antimicrobial influx and efflux. PMID:26528273

Colonic catabolism of dietary phenolic and polyphenolic compounds from Concord grape juice.

PubMed

Stalmach, Angelique; Edwards, Christine A; Wightman, Jolynne D; Crozier, Alan

2013-01-01

After acute ingestion of 350 ml of Concord grape juice, containing 528 μmol of (poly)phenolic compounds, by healthy volunteers, a wide array of phase I and II metabolites were detected in the circulation and excreted in urine. Ingestion of the juice by ileostomists resulted in 40% of compounds being recovered intact in ileal effluent. The current study investigated the fate of these undigested (poly)phenolic compounds on reaching the colon. This was achieved through incubation of the juice using an in vitro model of colonic fermentation and through quantification of catabolites produced after colonic degradation and their subsequent absorption prior to urinary excretion by healthy subjects and ileostomy volunteers. A total of 16 aromatic and phenolic compounds derived from colonic metabolism of Concord grape juice (poly)phenolic compounds were identified by GC-MS in the faecal incubation samples. Thirteen urinary phenolic acids and aromatic compounds were excreted in significantly increased amounts after intake of the juice by healthy volunteers, whereas only two of these compounds were excreted in elevated amounts by ileostomists. The production of phenolic acids and aromatic compounds by colonic catabolism contributed to the bioavailability of Concord grape (poly)phenolic compounds to a much greater extent than phase I and II metabolites originating from absorption in the upper gastrointestinal tract. Catabolic pathways are proposed, highlighting the impact of colonic microbiota and subsequent phase II metabolism prior to excretion of phenolic compounds derived from (poly)phenolic compounds in Concord grape juice, which pass from the small to the large intestine.

Recycling of phenolic compounds in Borneo's tropical peat swamp forests.

PubMed

Yule, Catherine M; Lim, Yau Yan; Lim, Tse Yuen

2018-02-07

Tropical peat swamp forests (TPSF) are globally significant carbon stores, sequestering carbon mainly as phenolic polymers and phenolic compounds (particularly as lignin and its derivatives) in peat layers, in plants, and in the acidic blackwaters. Previous studies show that TPSF plants have particularly high levels of phenolic compounds which inhibit the decomposition of organic matter and thus promote peat accumulation. The studies of phenolic compounds are thus crucial to further understand how TPSF function with respect to carbon sequestration. Here we present a study of cycling of phenolic compounds in five forests in Borneo differing in flooding and acidity, leaching of phenolic compounds from senescent Macaranga pruinosa leaves, and absorption of phenolics by M. pruinosa seedlings. The results of the study show that total phenolic content (TPC) in soil and leaves of three species of Macaranga were highest in TPSF followed by freshwater swamp forest and flooded limestone forest, then dry land sites. Highest TPC values were associated with acidity (in TPSF) and waterlogging (in flooded forests). Moreover, phenolic compounds are rapidly leached from fallen senescent leaves, and could be reabsorbed by tree roots and converted into more complex phenolics within the leaves. Extreme conditions-waterlogging and acidity-may facilitate uptake and synthesis of protective phenolic compounds which are essential for impeded decomposition of organic matter in TPSF. Conversely, the ongoing drainage and degradation of TPSF, particularly for conversion to oil palm plantations, reverses the conditions necessary for peat accretion and carbon sequestration.

Directional liquefaction of biomass for phenolic compounds and in situ hydrodeoxygenation upgrading of phenolics using bifunctional catalysts

Treesearch

Junfeng Feng; Chung-yun Hse; Kui Wang; Zhongzhi Yang; Jianchun Jiang; Junming Xu

2017-01-01

Phenolic compounds derived from biomass are important feedstocks for the sustainable production of hydrocarbon biofuels. Hydrodeoxygenation is an effective process to remove oxygen-containing functionalities in phenolic compounds. This paper reported a simple method for producing hydrocarbons by liquefying biomass and upgrading liquefied products. Three phenolic...

Genetic evidence for direct sensing of phenolic compounds by the VirA protein of Agrobacterium tumefaciens.

PubMed Central

Lee, Y W; Jin, S; Sim, W S; Nester, E W

1995-01-01

The virulence (vir) genes of Agrobacterium tumefaciens are induced by low-molecular-weight phenolic compounds and monosaccharides through a two-component regulatory system consisting of the VirA and VirG proteins. However, it is not clear how the phenolic compounds are sensed by the VirA/VirG system. We tested the vir-inducing abilities of 15 different phenolic compounds using four wild-type strains of A. tumefaciens--KU12, C58, A6, and Bo542. We analyzed the relationship between structures of the phenolic compounds and levels of vir gene expression in these strains. In strain KU12, vir genes were not induced by phenolic compounds containing 4'-hydroxy, 3'-methoxy, and 5'-methoxy groups, such as acetosyringone, which strongly induced vir genes of the other three strains. On the other hand, vir genes of strain KU12 were induced by phenolic compounds containing only a 4'-hydroxy group, such as 4-hydroxyacetophenone, which did not induce vir genes of the other three strains. The vir genes of strains KU12, A6, and Bo542 were all induced by phenolic compounds containing 4'-hydroxy and 3'-methoxy groups, such as acetovanillone. By transferring different Ti plasmids into isogenic chromosomal backgrounds, we showed that the phenolic-sensing determinant is associated with Ti plasmid. Subcloning of Ti plasmid indicates that the virA locus determines which phenolic compounds can function as vir gene inducers. These results suggest that the VirA protein directly senses the phenolic compounds for vir gene activation. PMID:8618878

Food processing strategies to enhance phenolic compounds bioaccessibility and bioavailability in plant-based foods.

PubMed

Ribas-Agustí, Albert; Martín-Belloso, Olga; Soliva-Fortuny, Robert; Elez-Martínez, Pedro

2017-06-13

Phenolic compounds are important constituents of plant-based foods, as their presence is related to protective effects on health. To exert their biological activity, phenolic compounds must be released from the matrix during digestion in an absorbable form (bioaccessible) and finally absorbed and transferred to the bloodstream (bioavailable). Chemical structure and matrix interactions are some food-related factors that hamper phenolic compounds bioaccessibility and bioavailability, and that can be counteracted by food processing. It has been shown that food processing can induce chemical or physical modifications in food that enhance phenolic compounds bioaccessibility and bioavailability. These changes include: (i) chemical modifications into more bioaccessible and bioavailable forms; (ii) cleavage of covalent or hydrogen bonds or hydrophobic forces that attach phenolic compounds to matrix macromolecules; (iii) damaging microstructural barriers such as cell walls that impede the release from the matrix; and (iv) create microstructures that protect phenolic compounds until they are absorbed. Indeed, food processing can produce degradation of phenolic compounds, however, it is possible to counteract it by modulating the operating conditions in favor of increased bioaccessibility and bioavailability. This review compiles the current knowledge on the effects of processing on phenolic compounds bioaccessibility or bioavailability, while suggesting new guidelines in the search of optimal processing conditions as a step forward towards the design of healthier foods.

Phenolic Compounds in the Potato and Its Byproducts: An Overview

PubMed Central

Akyol, Hazal; Riciputi, Ylenia; Capanoglu, Esra; Caboni, Maria Fiorenza; Verardo, Vito

2016-01-01

The potato (Solanum tuberosum L.) is a tuber that is largely used for food and is a source of different bioactive compounds such as starch, dietary fiber, amino acids, minerals, vitamins, and phenolic compounds. Phenolic compounds are synthetized by the potato plant as a protection response from bacteria, fungi, viruses, and insects. Several works showed that these potato compounds exhibited health-promoting effects in humans. However, the use of the potato in the food industry submits this vegetable to different processes that can alter the phenolic content. Moreover, many of these compounds with high bioactivity are located in the potato’s skin, and so are eliminated as waste. In this review the most recent articles dealing with phenolic compounds in the potato and potato byproducts, along with the effects of harvesting, post-harvest, and technological processes, have been reviewed. Briefly, the phenolic composition, main extraction, and determination methods have been described. In addition, the “alternative” food uses and healthy properties of potato phenolic compounds have been addressed. PMID:27240356

A comprehensive evaluation of three microfluidic chemiluminescence methods for the determination of the total phenolic contents in fruit juices.

PubMed

Al Haddabi, Buthaina; Al Lawati, Haider A J; Suliman, FakhrEldin O

2017-01-01

Three recently reported microfluidic chemiluminescence (MF-CL) methods (based on reactions with acidic permanganate enhanced by formaldehyde (KMnO4-COH), acidic cerium (IV) and rhodamine B (Ce-RB), and acidic cerium (IV) and rhodamine 6G (Ce-R6G) enhanced by SDS) for the determination of the total phenolic content (TPC) in juices were critically evaluated in terms of their selectivity. The evaluation was carried out using 86 analytes, including 22 phenolic compounds (phenolic acids and polyphenols), 6 known non-phenolic antioxidants, 9 amino acids and a number of proteins, carbohydrates, nucleotide bases, inorganic salts and other compounds. Each method was sensitive toward phenolic compounds (PCs). However, the KMnO4-COH CL system showed a higher sensitivity toward phenolic acids and also responded to non-phenolic antioxidants. The other two systems showed higher sensitivity toward polyphenolic compounds than to phenolic acids and did not responded to all other compounds including non-phenolic antioxidants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: characterization by high-performance liquid chromatography-diode array detection-electrospray tandem mass spectrometry.

PubMed

Magalhães, Paulo J; Vieira, Joana S; Gonçalves, Luís M; Pacheco, João G; Guido, Luís F; Barros, Aquiles A

2010-05-07

The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP) and subsequent desorption of the adsorbed polyphenols with acetone/water (70:30, v/v). At last, the extract was analyzed by HPLC-DAD and HPLC-ESI-MS/MS. The first phase of this work consisted of the study of the adsorption behavior of several classes of phenolic compounds (e.g. phenolic acids, flavonols, and flavanols) by PVPP in model solutions. It has been observed that the process of adsorption of the different phenolic compounds to PVPP (at low concentrations) is differentiated, depending on the structure of the compound (number of OH groups, aromatic rings, and stereochemistry hindrance). For example, within the phenolic acids class (benzoic, p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (>or=80%) and recovery yield values (>or=70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC-DAD and HPLC-ESI-MS/MS. Copyright (c) 2009 Elsevier B.V. All rights reserved.

Phenolic content variability and its chromosome location in tritordeum

PubMed Central

Navas-Lopez, José F.; Ostos-Garrido, Francisco J.; Castillo, Almudena; Martín, Antonio; Gimenez, Maria J.; Pistón, Fernando

2014-01-01

For humans, wheat is the most important source of calories, but it is also a source of antioxidant compounds that are involved in the prevention of chronic disease. Among the antioxidant compounds, phenolic acids have great potential to improve human health. In this paper we evaluate the effect of environmental and genetic factors on the phenolics content in the grain of a collection of tritordeums with different cytoplasm and chromosome substitutions. To this purpose, tritordeum flour was used for extraction of the free, conjugates and bound phenolic compounds. These phenolic compounds were identified and quantified by RP-HPLC and the results were analyzed by univariate and multivariate methods. This is the first study that describes the composition of phenolic acids of the amphiploid tritordeum. As in wheat, the predominant phenolic compound is ferulic acid. In tritordeum there is great variability for the content of phenolic compounds and the main factor which determines its content is the genotype followed by the environment, in this case included in the year factor. Phenolic acid content is associated with the substitution of chromosome DS1D(1Hch) and DS2D(2Hch), and the translocation 1RS/1BL in tritordeum. The results show that there is high potential for further improving the quality and quantity of phenolics in tritordeum because this amphiploid shows high variability for the content of phenolic compounds. PMID:24523725

Comparative evaluation of maceration and ultrasonic-assisted extraction of phenolic compounds from fresh olives.

PubMed

Deng, Junlin; Xu, Zhou; Xiang, Chunrong; Liu, Jing; Zhou, Lijun; Li, Tian; Yang, Zeshen; Ding, Chunbang

2017-07-01

Ultrasonic-assisted extraction (UAE) and maceration extraction (ME) were optimized using response surface methodology (RSM) for total phenolic compounds (TPC) from fresh olives. The main phenolic compounds and antioxidant activity of TPC were also investigated. The optimized result for UAE was 22mL/g of liquid-solid ratio, 47°C of extraction temperature and 30min of extraction time, 7.01mg/g of yielding, and for ME was 24mL/g of liquid-solid ratio, 50°C of extraction temperature and 4.7h of extraction time, 5.18mg/g of yielding. The HPLC analysis revealed that the extracts by UAE and ME possessed 14 main phenolic compounds, and UAE exhibited more amounts of all phenols than ME. The most abundant phenolic compounds in olive extracts were hydroxytyrosol, oleuropein and rutin. Both extracts showed excellent antioxidant activity in a dose-dependent manner. Taken together, UAE could effectively increase the yield of phenolic compounds from olives. In addition these phenolic compounds could be used as a potential source of natural antioxidants. Copyright © 2017 Elsevier B.V. All rights reserved.

Effect of solvent on the extraction of phenolic compounds and antioxidant capacity of hazelnut kernel.

PubMed

Fanali, Chiara; Tripodo, Giusy; Russo, Marina; Della Posta, Susanna; Pasqualetti, Valentina; De Gara, Laura

2018-03-22

Hazelnut kernel phenolic compounds were recovered applying two different extraction approaches, namely ultrasound-assisted solid/liquid extraction (UA-SLE) and solid-phase extraction (SPE). Different solvents were tested evaluating total phenolic compounds and total flavonoids contents together to antioxidant activity. The optimum extraction conditions, in terms of the highest value of total phenolic compounds extracted together to other parameters like simplicity and cost were selected for method validation and individual phenolic compounds analysis. The UA-SLE protocol performed using 0.1 g of defatted sample and 15 mL of extraction solvent (1 mL methanol/1 mL water/8 mL methanol 0.1% formic acid/5 mL acetonitrile) was selected. The analysis of hazelnut kernel individual phenolic compounds was obtained by HPLC coupled with DAD and MS detections. Quantitative analysis was performed using a mixture of six phenolic compounds belonging to phenolic classes' representative of hazelnut. Then, the method was fully validated and the resulting RSD% values for retention time repeatability were below 1%. A good linearity was obtained giving R 2 no lower than 0.997.The accuracy of the extraction method was also assessed. Finally, the method was applied to the analysis of phenolic compounds in three different hazelnut kernel varieties observing a similar qualitative profile with differences in the quantity of detected compounds. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Plant phenolic compounds and oxidative stress: integrated signals in fungal-plant interactions.

PubMed

Shalaby, Samer; Horwitz, Benjamin A

2015-08-01

Upon invasion of a host, fungal pathogens are exposed to a variety of stresses. Plants release reactive oxygen species, and mount a variety of preformed and induced chemical defenses. Phenolic compounds are one example: they are ubiquitous in plants, and an invading pathogen encounters them already at the leaf surface, or for soil-borne pathogens, in the rhizosphere. Phenolic and related aromatic compounds show varying degrees of toxicity to cells. Some compounds are quite readily metabolized, and others less so. It was known already from classical studies that phenolic substrates induce the expression of the enzymes for their degradation. Recently, the ability to degrade phenolics was shown to be a virulence factor. Conversely, phenolic compounds can increase the effectiveness of antifungals. Phenolics are known antioxidants, yet they have been shown to elicit cellular responses that would usually be triggered to counter oxidant stress. Here, we review the evidence for a connection between the fungal response to phenolics as small-molecule signals, and the response to oxidants. The connections proposed here should enable genetic screens to identify specific fungal receptors for plant phenolics. Furthermore, understanding how the pathogen detects plant phenolic compounds as a stress signal may facilitate new antifungal strategies.

Phenolic metabolites in leaves of the invasive shrub, Lonicera maackii, and their potential phytotoxic and anti-herbivore effects.

PubMed

Cipollini, Don; Stevenson, Randall; Enright, Stephanie; Eyles, Alieta; Bonello, Pierluigi

2008-02-01

Lonicera maackii is an invasive shrub in North America for which allelopathic effects toward other plants or herbivores have been suspected. We characterized the major phenolic metabolites present in methanol extracts of L. maackii leaves. In addition, we examined the effects of methanol-water extracts of L. maackii leaves on seed germination of a target plant species and on feeding preference and growth rate of a generalist insect herbivore. A total of 13 individual major and minor compounds were detected in crude leaf extracts by high-performance liquid chromatography coupled to electronspray ionization-tandem mass spectrometry (ESI-MS/MS). Extracts were dominated by two major flavones, apigenin and luteolin, and their glucoside derivatives, apigenin-7-glucoside and luteolin-7-glucoside. Quantities of these compounds, along with chlorogenic acid, varied between two sampling points. Leaf extracts that contained these compounds were inhibitory to seed germination of Arabidopsis thaliana. In addition, treatment of artificial diet with leaf extracts deterred feeding of the generalist herbivore, Spodoptera exigua, in choice experiments but had no effect on growth rate in short-term no-choice bioassays. Purified apigenin tended to deter feeding by S. exigua and inhibited seed germination of A. thaliana. We conclude that leaves of L. maackii contain phenolic compounds, including apigenin and chlorogenic acid, capable of having biological effects on other plants and insects.

Laccase enzyme detoxifies hydrolysates and improves biogas production from hemp straw and miscanthus.

PubMed

Schroyen, Michel; Van Hulle, Stijn W H; Holemans, Sander; Vervaeren, Han; Raes, Katleen

2017-11-01

The impact of various phenolic compounds, vanillic acid, ferulic acid, p-coumaric acid and 4-hydroxybenzoic acid on anaerobic digestion of lignocellulosic biomass (hemp straw and miscanthus) was studied. Such phenolic compounds have been known to inhibit biogas production during anaerobic digestion. The different phenolic compounds were added in various concentrations: 0, 100, 500, 1000 and 2000mg/L. A difference in inhibition of biomethane production between the phenolic compounds was noted. Hydrolysis rate, during anaerobic digestion of miscanthus was inhibited up to 50% by vanillic acid, while vanillic acid had no influence on the initial rate of biogas production during the anaerobic digestion of hemp straw. Miscanthus has a higher lignin concentration (12-30g/100gDM) making it less accessible for degradation, and in combination with phenolic compounds released after harsh pretreatments, it can cause severe inhibition levels during the anaerobic digestion, lowering biogas production. To counter the inhibition, lignin degrading enzymes can be used to remove or degrade the inhibitory phenolic compounds. The interaction of laccase and versatile peroxidase individually with the different phenolic compounds was studied to have insight in the polymerization of inhibitory compounds or breakdown of lignocellulose. Hemp straw and miscanthus were incubated with 0, 100 and 500mg/L of the different phenolic compounds for 0, 6 and 24h and pretreated with the lignin degrading enzymes. A laccase pretreatment successfully detoxified the substrate, while versatile peroxidase however was inhibited by 100mg/L of each of the individual phenolic compounds. Finally a combination of enzymatic detoxification and subsequent biogas production showed that a decrease in phenolic compounds by laccase treatment can considerably lower the inhibition levels of the biogas production. Copyright © 2017 Elsevier Ltd. All rights reserved.

Predicting the reactivity of adhesive starting materials

Treesearch

Anthony H. Conner

1999-01-01

Phenolic compounds are important in the production of bonded-wood products. Phenolic compounds in addition to phenol and resorcinol are potential alternative feedstocks for producing adhesives. The reactivity of a wide variety of phenolic compounds with formaldehyde was investigated using semi-empirical and ab initio computational chemistry methods...

From Olive Fruits to Olive Oil: Phenolic Compound Transfer in Six Different Olive Cultivars Grown under the Same Agronomical Conditions.

PubMed

Talhaoui, Nassima; Gómez-Caravaca, Ana María; León, Lorenzo; De la Rosa, Raúl; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-03-04

Phenolic compounds are responsible of the nutritional and sensory quality of extra-virgin olive oil (EVOO). The composition of phenolic compounds in EVOO is related to the initial content of phenolic compounds in the olive-fruit tissues and the activity of enzymes acting on these compounds during the industrial process to produce the oil. In this work, the phenolic composition was studied in six major cultivars grown in the same orchard under the same agronomical and environmental conditions in an effort to test the effects of cultivars on phenolic composition in fruits and oils as well as on transfer between matrices. The phenolic fractions were identified and quantified using high-performance liquid chromatography-diode array detector-time-of-flight-mass spectrometry. A total of 33 phenolic compounds were determined in the fruit samples and a total of 20 compounds in their corresponding oils. Qualitative and quantitative differences in phenolic composition were found among cultivars in both matrices, as well as regarding the transfer rate of phenolic compounds from fruits to oil. The results also varied according to the different phenolic groups evaluated, with secoiridoids registering the highest transfer rates from fruits to oils. Moreover, wide-ranging differences have been noticed between cultivars for the transfer rates of secoiridoids (4.36%-65.63% of total transfer rate) and for flavonoids (0.18%-0.67% of total transfer rate). 'Picual' was the cultivar that transferred secoiridoids to oil at the highest rate, whereas 'Changlot Real' was the cultivar that transferred flavonoids at the highest rates instead. Principal-component analysis confirmed a strong genetic effect on the basis of the phenolic profile both in the olive fruits and in the oils.

Extensive characterisation of bioactive phenolic constituents from globe artichoke (Cynara scolymus L.) by HPLC-DAD-ESI-QTOF-MS.

PubMed

Abu-Reidah, Ibrahim M; Arráez-Román, David; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

2013-12-01

The aim of this work was to characterise the phenolic compounds in artichoke (hearts) by using HPLC coupled to DAD-ESI-QTOF-MS, which proved useful in characterising 61 phenolic and other polar compounds. Notably, of the 61 compounds characterised, 34 new phenolic compounds with their isomers have been tentatively characterised in artichoke for the first time, namely: 3 hydroxybenzoic acids, 17 hydroxycinnamic acids, 4 lignans, 7 flavones, 2 flavonols, and 1 phenol derivative. Moreover, a total of 28 isomers of previously described phenolics have also been detected. The data compiled from the qualitative polyphenol characterisation indicate that the artichoke extract analysed (Blanca de Tudela variety) could be regarded as a bioactive functional food and also as a promising source of antioxidant phenolic compounds. Copyright © 2013 Elsevier Ltd. All rights reserved.

Comparative Analysis of Chemical Composition, Antioxidant Activity and Quantitative Characterization of Some Phenolic Compounds in Selected Herbs and Spices in Different Solvent Extraction Systems.

PubMed

Sepahpour, Shabnam; Selamat, Jinap; Abdul Manap, Mohd Yazid; Khatib, Alfi; Abdull Razis, Ahmad Faizal

2018-02-13

This study evaluated the efficacy of various organic solvents (80% acetone, 80% ethanol, 80% methanol) and distilled water for extracting antioxidant phenolic compounds from turmeric, curry leaf, torch ginger and lemon grass extracts. They were analyzed regarding the total phenol and flavonoid contents, antioxidant activity and concentration of some phenolic compounds. Antioxidant activity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay and the ferric reducing antioxidant power (FRAP) assay. Quantification of phenolic compounds was carried out using high-performance liquid chromatography (HPLC). All the extracts possessed antioxidant activity, however, the different solvents showed different efficiencies in the extraction of phenolic compounds. Turmeric showed the highest DPPH values (67.83-13.78%) and FRAP (84.9-2.3 mg quercetin/g freeze-dried crude extract), followed by curry leaf, torch ginger and lemon grass. While 80% acetone was shown to be the most efficient solvent for the extraction of total phenolic compounds from turmeric, torch ginger and lemon grass (221.68, 98.10 and 28.19 mg GA/g freeze dried crude extract, respectively), for the recovery of phenolic compounds from curry leaf (92.23 mg GA/g freeze-dried crude extract), 80% ethanol was the most appropriate solvent. Results of HPLC revealed that the amount of phenolic compounds varied depending on the types of solvents used.

Phenolic Molding Compounds

NASA Astrophysics Data System (ADS)

Koizumi, Koji; Charles, Ted; de Keyser, Hendrik

Phenolic Molding Compounds continue to exhibit well balanced properties such as heat resistance, chemical resistance, dimensional stability, and creep resistance. They are widely applied in electrical, appliance, small engine, commutator, and automotive applications. As the focus of the automotive industry is weight reduction for greater fuel efficiency, phenolic molding compounds become appealing alternatives to metals. Current market volumes and trends, formulation components and its impact on properties, and a review of common manufacturing methods are presented. Molding processes as well as unique advanced techniques such as high temperature molding, live sprue, and injection/compression technique provide additional benefits in improving the performance characterisitics of phenolic molding compounds. Of special interest are descriptions of some of the latest innovations in automotive components, such as the phenolic intake manifold and valve block for dual clutch transmissions. The chapter also characterizes the most recent developments in new materials, including long glass phenolic molding compounds and carbon fiber reinforced phenolic molding compounds exhibiting a 10-20-fold increase in Charpy impact strength when compared to short fiber filled materials. The role of fatigue testing and fatigue fracture behavior presents some insight into long-term reliability and durability of glass-filled phenolic molding compounds. A section on new technology outlines the important factors to consider in modeling phenolic parts by finite element analysis and flow simulation.

Antibacterial activity of sphagnum acid and other phenolic compounds found in Sphagnum papillosum against food-borne bacteria.

PubMed

Mellegård, H; Stalheim, T; Hormazabal, V; Granum, P E; Hardy, S P

2009-07-01

To identify the phenolic compounds in the leaves of Sphagnum papillosum and examine their antibacterial activity at pH appropriate for the undissociated forms. Bacterial counts of overnight cultures showed that whilst growth of Staphylococcus aureus 50084 was impaired in the presence of milled leaves, the phenol-free fraction of holocellulose of S. papillosum had no bacteriostatic effect. Liquid chromatography-mass spectrometry analysis of an acetone-methanol extract of the leaves detected eight phenolic compounds. Antibacterial activity of the four dominating phenols specific to Sphagnum leaves, when assessed in vitro as minimal inhibitory concentrations (MICs), were generally >2.5 mg ml(-1). MIC values of the Sphagnum-specific compound 'sphagnum acid' [p-hydroxy-beta-(carboxymethyl)-cinnamic acid] were >5 mg ml(-1). No synergistic or antagonistic effects of the four dominating phenols were detected in plate assays. Sphagnum-derived phenolics exhibit antibacterial activity in vitro only at concentrations far in excess of those found in the leaves. We have both identified the phenolic compounds in S. papillosum and assessed their antibacterial activity. Our data indicate that phenolic compounds in isolation are not potent antibacterial agents and we question their potency against food-borne pathogens.

Comparison of the free and bound phenolic profiles and cellular antioxidant activities of litchi pulp extracts from different solvents

PubMed Central

2014-01-01

Background The phenolic contents and antioxidant activities of fruits could be underestimated if the bound phenolic compounds are not considered. In the present study, the extraction efficiencies of various solvents were investigated in terms of the total content of the free and bound phenolic compounds, as well as the phenolic profiles and antioxidant activities of the extracts. Methods Five different solvent mixtures were used to extract the free phenolic compounds from litchi pulp. Alkaline and acidic hydrolysis methods were compared for the hydrolysis of bound phenolic compounds from litchi pulp residue. The phenolic compositions of the free and bound fractions from the litchi pulp were identified using HPLC-DAD. The antioxidant activities of the litchi pulp extracts were determined by oxygen radical absorbance capacity (ORAC) and cellular antioxidant activity (CAA) assays. Results Of the solvents tested, aqueous acetone extracted the largest amount of total free phenolic compounds (210.7 mg GAE/100 g FW) from litchi pulp, followed sequentially by aqueous mixtures of methanol, ethanol and ethyl acetate, and water itself. The acid hydrolysis method released twice as many bound phenolic compounds as the alkaline hydrolysis method. Nine phenolic compounds were detected in the aqueous acetone extract. In contrast, not all of these compounds were found in the other four extracts. The classification and content of the bound phenolic compounds released by the acid hydrolysis method were higher than those achieved by the alkaline hydrolysis. The aqueous acetone extract showing the highest ORAC value (3406.9 μmol TE/100 g FW) for the free phenolic extracts. For the CAA method, however, the aqueous acetone and methanol extracts (56.7 and 55.1 μmol QE/100 g FW) showed the highest levels of activity of the five extracts tested. The ORAC and CAA values of the bound phenolic compounds obtained by acid hydrolysis were 2.6- and 1.9-fold higher than those obtained using the alkaline hydrolysis method. Conclusions The free and bound phenolic contents and profiles and antioxidant activities of the extracts were found to be dependent on the extraction solvent used. Litchi exhibited good cellular antioxidant activity and could be a potentially useful natural source of antioxidants. PMID:24405977

Content of different groups of phenolic compounds in microshoots of Juglans regia cultivars and studies on antioxidant activity

USDA-ARS?s Scientific Manuscript database

Phenolic and other compounds were extracted from micropropagated axillary shoots (microshoots) of the walnut (Juglans regia L.) cultivars ‘Chandler’, ‘Howard’, ‘Kerman’, ‘Sunland’, and ‘Z63’. Among cultivars, microshoots showed differences in phenolic compounds, phenolic acids, flavonoids and proant...

Olive Tree (Olea europeae L.) Leaves: Importance and Advances in the Analysis of Phenolic Compounds

PubMed Central

Abaza, Leila; Taamalli, Amani; Nsir, Houda; Zarrouk, Mokhtar

2015-01-01

Phenolic compounds are becoming increasingly popular because of their potential role in contributing to human health. Experimental evidence obtained from human and animal studies demonstrate that phenolic compounds from Olea europaea leaves have biological activities which may be important in the reduction in risk and severity of certain chronic diseases. Therefore, an accurate profiling of phenolics is a crucial issue. In this article, we present a review work on current treatment and analytical methods used to extract, identify, and/or quantify phenolic compounds in olive leaves. PMID:26783953

Phenolic Compounds Analysis of Root, Stalk, and Leaves of Nettle

PubMed Central

Otles, Semih; Yalcin, Buket

2012-01-01

Types of nettles (Urtica dioica) were collected from different regions to analyze phenolic compounds in this research. Nettles are specially grown in the coastal part. According to this kind of properties, nettle samples were collected from coastal part of (Mediterranean, Aegean, Black sea, and Marmara) Turkey. Phenolic profile, total phenol compounds, and antioxidant activities of nettle samples were analyzed. Nettles were separated to the part of root, stalk, and leaves. Then, these parts of nettle were analyzed to understand the difference of phenolic compounds and amount of them. Nettle (root, stalk and leaves) samples were analyzed by using High-Performance Liquid Chromatography with Diode-Array Detection (HPLC-DAD) to qualitative and quantitative determination of the phenolic compounds. Total phenolic components were measured by using Folin-Ciocalteu method. The antioxidant activity was measured by using DPPH (2,2-diphenyl-1-picrylhydrazyl) which is generally used for herbal samples and based on single electron transfer (SET). PMID:22593694

Phenolic compounds analysis of root, stalk, and leaves of nettle.

PubMed

Otles, Semih; Yalcin, Buket

2012-01-01

Types of nettles (Urtica dioica) were collected from different regions to analyze phenolic compounds in this research. Nettles are specially grown in the coastal part. According to this kind of properties, nettle samples were collected from coastal part of (Mediterranean, Aegean, Black sea, and Marmara) Turkey. Phenolic profile, total phenol compounds, and antioxidant activities of nettle samples were analyzed. Nettles were separated to the part of root, stalk, and leaves. Then, these parts of nettle were analyzed to understand the difference of phenolic compounds and amount of them. Nettle (root, stalk and leaves) samples were analyzed by using High-Performance Liquid Chromatography with Diode-Array Detection (HPLC-DAD) to qualitative and quantitative determination of the phenolic compounds. Total phenolic components were measured by using Folin-Ciocalteu method. The antioxidant activity was measured by using DPPH (2,2-diphenyl-1-picrylhydrazyl) which is generally used for herbal samples and based on single electron transfer (SET).

Inhibition and kinetic studies of cellulose- and hemicellulose-degrading enzymes of Ganoderma boninense by naturally occurring phenolic compounds.

PubMed

Surendran, A; Siddiqui, Y; Ali, N S; Manickam, S

2018-06-01

Ganoderma sp, the causal pathogen of the basal stem rot (BSR) disease of oil palm, secretes extracellular hydrolytic enzymes. These play an important role in the pathogenesis of BSR by nourishing the pathogen through the digestion of cellulose and hemicellulose of the host tissue. Active suppression of hydrolytic enzymes secreted by Ganoderma boninense by various naturally occurring phenolic compounds and estimation of their efficacy on pathogen suppression is focused in this study. Ten naturally occurring phenolic compounds were assessed for their inhibitory effect on the hydrolytic enzymes of G. boninense. The enzyme kinetics (V max and K m ) and the stability of the hydrolytic enzymes were also characterized. The selected compounds had shown inhibitory effect at various concentrations. Two types of inhibitions namely uncompetitive and noncompetitive were observed in the presence of phenolic compounds. Among all the phenolic compounds tested, benzoic acid was the most effective compound suppressive to the growth and production of hydrolytic enzymes secreted by G. boninense. The phenolic compounds as inhibitory agents can be a better replacement for the metal ions which are known as conventional inhibitors till date. The three hydrolytic enzymes were stable in a wide range of pH and temperature. These findings highlight the efficacy of the applications of phenolic compounds to control Ganoderma. The study has proved a replacement for chemical controls of G. boninense with naturally occurring phenolic compounds. © 2018 The Society for Applied Microbiology.

Lipid encapsulated phenolic compounds by fluidization

USDA-ARS?s Scientific Manuscript database

Phenolic compounds exhibit antioxidant and antimicrobial activities with applications as functional food and feed additives. Ferulic acid, a phenolic compound present in grain crops and lignocellulose biomass, was encapsulated with saturated triglycerides using a laboratory fluidizer. Stability of t...

Extracts of Phenolic Compounds from Seeds of Three Wild Grapevines—Comparison of Their Antioxidant Activities and the Content of Phenolic Compounds

PubMed Central

Weidner, Stanisław; Powałka, Anna; Karamać, Magdalena; Amarowicz, Ryszard

2012-01-01

Phenolic compounds were extracted from three wild grapevine species: Vitis californica, V. riparia and V. amurensis seeds using 80% methanol or 80% acetone. The total content of phenolic compounds was determined utilizing the Folin-Ciocalteu’s phenol reagent while the content of tannins was assayed with the vanillin and BSA precipitation methods. Additionally, the DPPH free radical scavenging activity and the reduction power of the extracts were measured. The RP-HPLC method was applied to identify the phenolic compounds in the extracts, such as phenolic acids and catechins. The seeds contained large amounts of tannins, catechins and gallic acid and observable quantities of p-coumaric acid. The total content of phenolic compounds and tannins was similar in the extracts from V. californica and V. riparia seeds. However, the total content of total phenolic compounds and tannins in the extracts from V. californica and V. riperia seeds were about two-fold higher than that in the extracts from V. amurensis seeds. Extracts from seeds of the American species (V. californica and V. riparia) contained similarly high concentrations of tannins, whereas extracts from seeds of V. amurensis had approximately half that amount of these compounds. The content of catechin and epicatechin was similar in all extracts. The highest DPPH• anti-radical scavenging activity was observed in the acetonic and methanolic extracts of V. californica and V. riparia seeds— while the acetonic extract from the V. californica seeds was the strongest reducing agent. PMID:22489161

The reactivity of phenolic and non-phenolic residual kraft lignin model compounds with Mn(II)-peroxidase from Lentinula edodes.

PubMed

Crestini, C; D'Annibale, A; Sermanni, G G; Saladino, R

2000-02-01

Three phenolic model compounds representing bonding patterns of residual kraft lignin were incubated with manganese peroxidase from Lentinula edodes. Extensive degradation of all the phenolic models, mainly occurring via side-chain benzylic oxidation, was observed. Among the tested model compounds the diphenylmethane alpha-5 phenolic model was found to be the most reactive, yielding several products showing oxidation and fragmentation at the bridging position. The non-phenolic 5-5' biphenyl and 5-5' diphenylmethane models were found unreactive.

In situ catalytic hydrogenation of model compounds and biomass-derived phenolic compounds for bio-oil upgrading

Treesearch

Junfeng Feng; Zhongzhi Yang; Chung-yun Hse; Qiuli Su; Kui Wang; Jianchun Jiang; Junming Xu

2017-01-01

The renewable phenolic compounds produced by directional liquefaction of biomass are a mixture of complete fragments decomposed from native lignin. These compounds are unstable and difficult to use directly as biofuel. Here, we report an efficient in situ catalytic hydrogenation method that can convert phenolic compounds into saturated cyclohexanes. The process has...

Effect of Sterilization Process and Storage on the Antioxidative Properties of Runner Bean.

PubMed

Wołosiak, Rafał; Drużyńska, Beata; Piecyk, Małgorzata; Majewska, Ewa; Worobiej, Elwira

2018-06-11

In this study, we investigated the effect of standard preservation of bean seeds on changes in contents and activity of their selected components: dry matter, ash, different forms of nitrogen, composition of protein fractions; total phenolics and condensed tannins; ability to chelate iron(II) ions; antiradical activity against ABTS •+ and DPPH • ; and capability for inhibiting autoxidation and enzymatic oxidation of linoleic acid. The conducted technological process caused various changes in contents of nitrogen forms and partial loss of phenolic compounds. The antiradical and antioxidative activity of the extracts decreased significantly, while an increase was observed in their ability to chelate Fe(II). These changes were due to the migration of active compounds to the brine, and to their structural transformations and degradation. Longer storage of the sterilized product caused restoration of part of the antiradical activity of the seeds.

Oxidative stability, phenolic compounds and antioxidant potential of a virgin olive oil enriched with natural bioactive compounds.

PubMed

Delgado-Adámez, Jonathan; Baltasar, M Nieves Franco; Yuste, María Concepción Ayuso; Martín-Vertedor, Daniel

2014-01-01

The aim of this research was to evaluate strategies for the development of a virgin olive oil (VOO) enriched with aqueous extracts of olive leaf and cake to increase the necessary dose in the diet of phenolic compounds with a natural product, as phenolic compounds are involved on the healthy properties of olive oil. Different extraction procedures were evaluated with the aim of increasing the phenol content and antioxidant potential of extracts of olive leaf and cake. As leaves extract presented a higher total phenolic content, it was characterized in order to determine its phenolic profile, and was employed to enrich VOO. Diverse procedures were used to prepare enriched VOO with the leaves extract, and finally the effects of phenol enrichment were evaluated based on the antioxidant potential and oxidative stability of the prepared phenol-enriched virgin olive oils. These enriched VOOs increased significantly the content in phenolic compounds, antioxidant potential and oxidative stability 40, 4 and 1.5 fold more, respectively, than the Control oil. Furthermore, the addition of lecithin had a positive effect both on the phenolic compounds content, and on the antioxidant potential of the oils. Besides, the use of the olive leaves extract, with and without lecithin respectively, supposes a strategy potential for reducing the harmful effects that inflicts long-term preservation of VOOs and its possible deterioration.

An Innovative Porous Nanocomposite Material for the Removal of Phenolic Compounds from Aqueous Solutions.

PubMed

Turco, Antonio; Monteduro, Anna Grazia; Mazzotta, Elisabetta; Maruccio, Giuseppe; Malitesta, Cosimino

2018-05-16

Energy efficient, low-cost, user-friendly, and green methods for the removal of toxic phenolic compounds from aqueous solution are necessary for waste treatment in industrial applications. Herein we present an interesting approach for the utilization of oxidized carbon nanotubes (CNTs) in the removal of phenolic compounds from aqueous solution. Dried pristine CNTs were stably incorporated in a solid porous support of polydimethylsiloxane (PDMS) facilitating the handling during both oxidation process of the nanomaterial and uptake of phenolic compounds, and enabling their safe disposal, avoiding expensive post-treatment processes. The adsorption studies indicated that the materials can efficiently remove phenolic compounds from water with different affinities towards different phenolic compounds. Furthermore, the adsorption kinetics and isotherms were studied in detail. The experimental data of adsorption fitted well with Langmuir and Freundlich isotherms, and pseudo-second-order kinetics, and the results indicated that the adsorption process was controlled by a two-step intraparticle diffusion model. The incorporation of CNTs in polymeric matrices did not affect their functionality in phenol uptake. The material was also successfully used for the removal of phenolic compounds from agricultural waste, suggesting its possible application in the treatment of wastewater. Moreover, the surface of the material could be regenerated, decreasing treatment costs.

Phenolic compound concentration and antioxidant activities of edible and medicinal mushrooms from Korea.

PubMed

Kim, Min-Young; Seguin, Philippe; Ahn, Joung-Kuk; Kim, Jong-Jin; Chun, Se-Chul; Kim, Eun-Hye; Seo, Su-Hyun; Kang, Eun-Young; Kim, Sun-Lim; Park, Yool-Jin; Ro, Hee-Myong; Chung, Ill-Min

2008-08-27

A study was conducted to determine the content of phenolic compounds and the antioxidative activity of five edible and five medicinal mushrooms commonly cultivated in Korea. Phenolic compounds were analyzed using high performance liquid chromatography, and antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity and superoxide dismutase activity. A total of 28 phenolic compounds were detected in the mushrooms studied. The average total concentration of phenolic compounds was 326 microg/g, the average being of 174 microg/g in edible mushrooms and 477 microg/g in medicinal mushrooms. The average total flavonoids concentration was 49 microg/g, with averages of 22 and 76 microg/g in edible and medicinal mushrooms, respectively. The DPPH radical scavenging activities ranged between 15 (Pleurotus eryngii) and 70% (Ganoderma lucidum) when reaction time was for 1 min. When reaction time was 30 min, the values ranged between 5 (Pleurotus eryngii) and 78% (Agaricus bisporus). The SOD activity averaged 28% among the 10 mushroom species, averages for edible and medicinal mushrooms being comparable. DPPH activities was significantly correlated (p < 0.01) with total content of phenolic compounds in edible mushrooms, while in medicinal mushrooms there was a significant correlation (p < 0.01) between SOD activity and total concentration of phenolic compounds. Numerous significant positive correlations were observed between phenolic compounds detected and antioxidative potential.

[Branch-specific detection of phenols and assessment of ground water solubility].

PubMed

Fischer, F; Kerndorff, H; Kühn, S

2000-01-01

There are about 500 technically relevant phenolic compounds such as cresols, chlorophenols or nitrophenols. It is most preferable to determine phenols as single compounds via gas chromatography. Further, phenols can also be assayed as photometrically as an overall parameter (Phenolindex): however, no conclusions about specific compounds can be drawn from this type of test. Also this method is not as reliable for an hazard assessment as gas chromatography. First, not all phenols, for instance resorcinol or 1-naphthol can be determined with this method. Second, phenolic groups in humic substances, which do not constitute a threat for groundwater, are determined alongside environmentally relevant phenols using this method. In most cases, it is possible to deduce which phenols can be expected in the groundwater of contaminated sites from the type of industrial usage, such as chlorophenols and pulp bleaching or nitrophenols and the production of explosives. Phenols are formed during coal combustion for instance at cokemanufactures or gasworks. They are important raw materials for the chemical industry from which resins, surfactants, pharmaceuticals, pigments, explosives, and stabilizers are produced. During the 80's phenol, cresols, nonylphenols, anisidines, aminophenols, dihydroxybenzenes, and naphthols were manufactured in amounts exceeding 10,000 t/a. Also, phenolic compounds are used as additives in many areas for example as solvents in the electric industry, in sawmills, papermanufacture, electroplating of metal sheets, as photographic developers, as textile dyes, or for the tanning of hydes. Due to the formation and use of phenols at industrial sites, groundwater contaminations are possible via infiltration through the unsaturated zone. Especially at gasworks and ammunition factories, groundwater contaminations with phenols have become known. In the vicinity of railway tracks and associated facillities contaminations due to the use of pesticides or mineral oils are possible. Input of phenols on agricultural lands can be caused by pesticides, sewage sludge or manure. The groundwater downstream of landfills often contains phenol, chlorophenols, cresols, and xylenols. The formation of phenol from other organic contaminants as benzene in groundwater has been reported. The potential for mobilization of phenols in the saturated zone can be estimated from their physical and chemical properties. Especially low molecular weight phenols are easily mobilized due to their high solubility in water and low potential for accumulation. These compounds are: phenol, cresols, xylenols, chlorophenols, hydroxybenzenes, nitrophenols, anisidines, aminophenols, anisol, 2-phenoxyethanol, and thiophenol. The stability of phenols under laboratory conditions varies. The complete mineralization depends mainly on the experimental set-up, i.e. nutrients, temperature, and type of inocula. The anaerobic degradation of phenols is generally slower than the aerobic. Phenol is readily biodegradable under both aerobic and anaerobic conditions. In general, the biodegradability depends on the type, number and position of substitutes. Phenols with nitro-, alkyl-, or chlorosubstitutes are more recalcitrant than phenol itself. Our biodegradability test show that the decomposition of alkylphenols is determined by the length and branching of the alcyllic chain. Phenols with high contamination potential are chlorophenols, xylenols, and nitrophenols. These compounds are both mobile and recalcitrant in the saturated zone. Phenolic compounds of a medium contamination risk are dichlorophenols, trichlorophenols, cresols, and phenol because they are mobile but less stable in groundwater. These compounds are known contaminants in the groundwater at gasworks, landfills, and ammunition factories. Aminophenols, anisidines, tert-butylphenols, ethylphenols, hydroxybenzenes, and 2-phenoxyethanol also constite a potential hazard for groundwater; however, no contaminations with these compounds are known. Poisoning due to oral uptake of phenol contaminated ground- or drinking water have not been reported, which might be due to the pungent odor and taste phenolic compounds have even at very low concentrations (mg/L). Because of the taste problem, the German drinking water standard for phenols is 0.5 microgram/L. In Berlin, groundwater with phenol concentrations higher than 30 micrograms/L of alkylphenols or 2 micrograms/L of chlorophenols is considered contaminated.

Predicting the reactivity of phenolic compounds with formaldehyde. II, continuation of an ab initio study.

Treesearch

Tohru Mitsunaga; Anthony H. Conner; Charles G. Jr. Hill

2002-01-01

Phenol–formaldehyde resins are important adhesives used by the forest products industry. The phenolic compounds in these resins are derived primarily from petrochemical sources. Alternate sources of phenolic compounds include tannins, lignins, biomass pyrolysis products, and coal gasification products. Because of variations in their chemical structures, the...

The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis

PubMed Central

Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

2016-01-01

Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves. PMID:27375495

The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis.

PubMed

Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

2016-01-01

Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves.

EVALUATION OF FREEZE DRIED ALOE VERA AND NOPAL CACTUS FOR POSSIBLE HEALTH TREATMENTS BY COMPARISON OF ANTIOXIDANT PROPERTIES AND FREE RADICAL INHIBITION.

PubMed

Rodriguez, Kenneth R; Jones, Anthony E; Belmont, Barbara

2014-01-01

The goal of this project was to characterize the antioxidant powers of lyophilized Aloe Vera ( Aloe barbadensis ) and Nopal Cactus (Opuntia ficus-indica) by quantifying the phenolics content and radical scavenging abilities of preparations derived from these plants. Extracts of these lyophylized succulents were assayed for phenolic compounds by the Folin Ciocalteau method and compared for free radical scavenging capability by the DPPH method. We found that even though the Aloe lyophilizate extract contained more phenolic content, the Nopal lyophilizate exhibited better free radical scavenging ability. Aloe Vera extract contained 0.278 g/L of phenolic content and exhibited 11.1% free radical inhibition, with a free radical scavenging rate constant of 0.177±0.015 min -1 . Nopal Cactus extract contained 0.174 g/L of phenolic content and exhibited 13.2% free radical inhibition, with a free radical scavenging rate constant of 0.155±0.009 min -1 . These results showed Nopal to have greater antioxidant potency than Aloe.

EVALUATION OF FREEZE DRIED ALOE VERA AND NOPAL CACTUS FOR POSSIBLE HEALTH TREATMENTS BY COMPARISON OF ANTIOXIDANT PROPERTIES AND FREE RADICAL INHIBITION

PubMed Central

Jones, Anthony E.; Belmont, Barbara

2016-01-01

The goal of this project was to characterize the antioxidant powers of lyophilized Aloe Vera (Aloe barbadensis) and Nopal Cactus (Opuntia ficus-indica) by quantifying the phenolics content and radical scavenging abilities of preparations derived from these plants. Extracts of these lyophylized succulents were assayed for phenolic compounds by the Folin Ciocalteau method and compared for free radical scavenging capability by the DPPH method. We found that even though the Aloe lyophilizate extract contained more phenolic content, the Nopal lyophilizate exhibited better free radical scavenging ability. Aloe Vera extract contained 0.278 g/L of phenolic content and exhibited 11.1% free radical inhibition, with a free radical scavenging rate constant of 0.177±0.015 min−1. Nopal Cactus extract contained 0.174 g/L of phenolic content and exhibited 13.2% free radical inhibition, with a free radical scavenging rate constant of 0.155±0.009 min−1. These results showed Nopal to have greater antioxidant potency than Aloe. PMID:27284273

Comparative phenolic compound profiles and antioxidative activity of the fruit, leaves, and roots of Korean ginseng (Panax ginseng Meyer) according to cultivation years

PubMed Central

Chung, Ill-Min; Lim, Ju-Jin; Ahn, Mun-Seob; Jeong, Haet-Nim; An, Tae-Jin; Kim, Seung-Hyun

2015-01-01

Background The study of phenolic compounds profiles and antioxidative activity in ginseng fruit, leaves, and roots with respect to cultivation years, and has been little reported to date. Hence, this study examined the phenolic compounds profiles and 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging activities in the fruit, leaves, and roots of Korean ginseng (Panax ginseng Meyer) as a function of cultivation year. Methods Profiling of 23 phenolic compounds in ginseng fruit, leaves, and roots was investigated using ultra-high performance liquid chromatography with the external calibration method. Antioxidative activity of ginseng fruit, leaves, and roots were evaluated using the method of DPPH free-radical-scavenging activity. Results The total phenol content in ginseng fruit and leaves was higher than in ginseng roots (p < 0.05), and the phenol content in the ginseng samples was significantly correlated to the DPPH free-radical-scavenging activity (r = 0.928****). In particular, p-coumaric acid (r = 0.847****) and ferulic acid (r = 0.742****) greatly affected the DPPH activity. Among the 23 phenolic compounds studied, phenolic acids were more abundant in ginseng fruit, leaves, and roots than the flavonoids and other compounds (p < 0.05). In particular, chlorogenic acid, gentisic acid, p- and m-coumaric acid, and rutin were the major phenolic compounds in 3–6-yr-old ginseng fruit, leaves, and roots. Conclusion This study provides basic information about the antioxidative activity and phenolic compounds profiles in fruit, leaves, and roots of Korean ginseng with cultivation years. This information is potentially useful to ginseng growers and industries involved in the production of high-quality and nutritional ginseng products. PMID:26843824

A review of phenolic compounds in oil-bearing plants: Distribution, identification and occurrence of phenolic compounds.

PubMed

Alu'datt, Muhammad H; Rababah, Taha; Alhamad, Mohammad N; Al-Mahasneh, Majdi A; Almajwal, Ali; Gammoh, Sana; Ereifej, Khalil; Johargy, Ayman; Alli, Inteaz

2017-03-01

Over the last two decades, separation, identification and measurement of the total and individual content of phenolic compounds has been widely investigated. Recently, the presence of a wide range of phenolic compounds in oil-bearing plants has been shown to contribute to their therapeutic properties, including anti-cancer, anti-viral, anti-oxidant, hypoglycemic, hypo-lipidemic, and anti-inflammatory activities. Phenolics in oil-bearing plants are now recognized as important minor food components due to several organoleptic and health properties, and they are used as food or sources of food ingredients. Variations in the content of phenolics in oil-bearing plants have largely been attributed to several factors, including the cultivation, time of harvest and soil types. A number of authors have suggested that the presence phenolics in extracted proteins, carbohydrates and oils may contribute to objectionable off flavors The objective of this study was to review the distribution, identification and occurrence of free and bound phenolic compounds in oil-bearing plants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Phenolic compounds extracted by acidic aqueous ethanol from berries and leaves of different berry plants.

PubMed

Tian, Ye; Liimatainen, Jaana; Alanne, Aino-Liisa; Lindstedt, Anni; Liu, Pengzhan; Sinkkonen, Jari; Kallio, Heikki; Yang, Baoru

2017-04-01

Phenolic compounds of berries and leaves of thirteen various plant species were extracted with aqueous ethanol and analyzed with UPLC-DAD-ESI-MS, HPLC-DAD, and NMR. The total content of phenolics was consistently higher in leaves than in berries (25-7856 vs. 28-711mg/100g fresh weight). Sea buckthorn leaves were richest in phenolic compounds (7856mg/100g f.w.) with ellagitannins as the dominant compound class. Sea buckthorn berries contained mostly isorhamnetin glycosides, whereas quercetin glycosides were typically abundant in most samples investigated. Anthocyanins formed the dominating group of phenolics in most dark-colored berries but phenolic acid derivatives were equally abundant in saskatoon and chokeberry berries. Caffeoylquinic acids constituted 80% of the total phenolic content (1664mg/100g f.w.) in bilberry leaves. B-type procyanidins and caffeoylquinic acids were the major phenolic compounds in hawthorn and rowanberry, respectively. Use of leaves of some species with prunasin, tyramine and β-p-arbutin, may be limited in food applications. Copyright © 2016 Elsevier Ltd. All rights reserved.

Spectroscopic analysis of phenolic compounds for food and feed formulations

USDA-ARS?s Scientific Manuscript database

Phenolic compounds exhibit several bioactive properties including anti-oxidant, anti-microbial, and anti-fungal characteristics with potential applications as additives in functional food and feed formulations. Phenolic compounds occur in plants as secondary metabolites and may be recovered as a co-...

Improve the biodegradability of post-hydrothermal liquefaction wastewater with ozone: conversion of phenols and N-heterocyclic compounds.

PubMed

Yang, Libin; Si, Buchun; Martins, Marcio Arêdes; Watson, Jamison; Chu, Huaqiang; Zhang, Yuanhui; Tan, Xiaobo; Zhou, Xuefei; Zhang, Yalei

2017-04-01

Hydrothermal liquefaction is a promising technology to convert wet biomass into bio-oil. However, post-hydrothermal liquefaction wastewater (PHWW) is also produced during the process. This wastewater contains a high concentration of organic compounds, including phenols and N-heterocyclic compounds which are two main inhibitors for biological treatment. Thus, proper treatment is required. In this work, ozone was used to convert phenols and N-heterocyclic compounds with a dosage range of 0-4.64 mg O 3 /mL PHWW. After ozone treatment, the phenols were fully converted, and acids were produced. However, N-heterocyclic compounds were found to have a low conversion rate (21.7%). The kinetic analysis for the degradation of phenols and N-heterocyclic compounds showed that the substitute played an important role in determining the priority of ozone reactions. The OH moiety in the ring compounds (phenols and pyridinol) may form hydroxyl radical, which lead to an efficient reaction. A substantial improved biodegradability of PHWW was observed after ozone treatment. The ratio of BOD 5 /COD was increased by about 32.36%, and reached a maximum of 0.41. The improved biodegradability of PHWW was justified by the conversion of phenols and N-heterocyclic compounds.

[Rapid analysis on phenolic compounds in Rheum palmatum based on UPLC-Q-TOF/MSE combined with diagnostic ions filter].

PubMed

Wang, Qing; Lu, Zhi-Wei; Liu, Yue-Hong; Wang, Ming-Ling; Fu, Shuang; Zhang, Qing-Qing; Zhao, Hui-Zhen; Zhang, Zhi-Xin; Xie, Zi-Ye; Huang, Zheng-Hai; Yu, Hong-Hong; Zhou, Wen-Juan; Gao, Xiao-Yan

2017-05-01

Diagnostic ions filter method was used to rapidly detect and identify the phenolic compounds in Rheum palmatum based on ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MSE). The representative authentic standards of phenolic compounds, including gallic acid, (+)-catechin, (－)-epicatechin, (－)-epicatechin-3-O-gallate and procyanidin B2, were subjected to analysis by UPLC-Q-TOF/MSE system with negative ion mode. Fragmentation patterns of each standard were summarized based on assigned fragment ions. The prominent product ions were selected as diagnostic ions. Subsequently, diagnostic ions filter was employed to rapidly recognize analogous skeletons. Combined with retention time, accurate mass, characteristic fragments and previous literature data, the structures of the filtered compounds were identified or tentatively characterized. A total 63 phenolic compounds (36 phenolic acid derivatives, 8 flavonoid derivatives and 19 tennis derivatives) in R. palmatum were identified, including 6 potential new compounds. The method of diagnostic ions filter could rapidly detect and identify phenolic compounds in R. palmatum This study provides a method for rapid detection of phenolic compounds in R. palmatum and is expected to complete the material basis of rhubarb. Copyright© by the Chinese Pharmaceutical Association.

Characterization of phenolic compounds in Pinus laricio needles and their responses to prescribed burnings.

PubMed

Cannac, Magali; Pasqualini, Vanina; Greff, Stéphane; Fernandez, Catherine; Ferrat, Lila

2007-07-30

Fire is a dominant ecological factor in Mediterranean-type ecosystems. Management strategies include prescribed (controlled) burning, which has been used in the management of several species, such as Pinus nigra ssp laricio var. Corsicana, a pine endemic to Corsica of great ecological and economic importance. The effects of prescribed burning on Pinus laricio have been little studied. The first aim of this study was to characterize total and simple phenolic compounds in Pinus laricio. The second aim was to understand: i) the short term (one to three months) and medium term (three years) effects of prescribed burning, and ii) the effects of periodic prescribed burning on the production of phenolic compounds in Pinus laricio. The first result of this study is the presence of total and simple phenolic compounds in the needles of Pinus laricio. 3-Vanillyl propanol is the major compound. After a prescribed burning, the synthesis of total phenolic compounds increases in Pinus laricio for a period of three months. Total phenolic compounds could be used as bioindicators for the short-term response of Pinus laricio needles to prescribed burning. Simple phenolic compounds do not seem to be good indicators of the impact of prescribed burning because prescribed burnings are low in intensity.

MICROBIAL METABOLISM OF AROMATIC COMPOUNDS I.

PubMed Central

Tabak, Henry H.; Chambers, Cecil W.; Kabler, Paul W.

1964-01-01

Tabak, Henry H. (Robert A. Taft Sanitary Engineering Center, Cincinnati, Ohio), Cecil W. Chambers, and Paul W. Kabler. Microbial metabolism of aromatic carbon compounds. I. Decomposition of phenolic compounds and aromatic hydrocarbons by phenol-adapted bacteria. J. Bacteriol. 87:910–919. 1964.—Bacteria from soil and related environments were selected or adapted to metabolize phenol, hydroxy phenols, nitrophenols, chlorophenols, methylphenols, alkylphenols, and arylphenols when cultured in mineral salts media with the specific substrate as the sole source of carbon. A phenol-adapted culture (substrate-induced enzyme synthesis proven) was challenged in respirometric tests with 104 related compounds; probable significant oxidative activity occurred with 65. Dihydric phenols were generally oxidized; trihydric phenols were not. Cresols and dimethylphenols were oxidized; adding a chloro group increased resistance. Benzoic and hydroxybenzoic acids were oxidized; sulfonated, methoxylated, nitro, and chlorobenzoic acids were not; m-toluic acid was utilized but not the o- and p-isomers. Benzaldehyde and p-hydroxybenzaldehyde were oxidized. In general, nitro- and chloro-substituted compounds and the benzenes were difficult to oxidize. PMID:14137630

Antioxidative activities and phenolic compounds of pumpkin (Cucurbita pepo) seeds and amaranth (Amaranthus caudatus) grain extracts.

PubMed

Peiretti, Pier Giorgio; Meineri, Giorgia; Gai, Francesco; Longato, Erica; Amarowicz, Ryszard

2017-09-01

Phenolic compounds were extracted from pumpkin (Cucurbita pepo) seed and amaranth (Amaranthus caudatus) grain into 80% (v/v) methanol. The extracts obtained were characterised by the contents of total phenolic compounds (TPC), trolox equivalent antioxidant capacity (TEAC), ferric-reducing antioxidant power (FRAP) and antiradical activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH · ) radical. The content of individual phenolic compounds was determined by HPLC-DAD method. Pumpkin seeds showed the higher content of TPC than that from amaranth. The TEAC values of both extracts were similar each other. The lower value of FRAP was observed for pumpkin seed. Phenolic compound present in amaranth grain exhibited strongest antiradical properties against DPPH radical. Several peaks were present on the HPLC chromatograms of two extracts. The UV-DAD spectra confirmed the presence of vanillic acid derivatives in the amaranth grain. The three main phenolic compound present in pumpkin seed were characterised by UV-DAD spectra with maximum at 258, 266 and 278 nm.

Utilizing a CdTe quantum dots-enzyme hybrid system for the determination of both phenolic compounds and hydrogen peroxide.

PubMed

Yuan, Jipei; Guo, Weiwei; Wang, Erkang

2008-02-15

In this paper, we attempt to construct a simple and sensitive detection method for both phenolic compounds and hydrogen peroxide, with the successful combination of the unique property of quantum dots and the specificity of enzymatic reactions. In the presence of H2O2 and horseradish peroxidase, phenolic compounds can quench quantum dots' photoluminescence efficiently, and the extent of quenching is severalfold to more than 100-fold increase. Quinone intermediates produced from the enzymatic catalyzed oxidation of phenolic compounds were believed to play the main role in the photoluminescence quenching. Using a quantum dots-enzyme system, the detection limits for phenolic compounds and hydrogen peroxide were detected to be approximately 10(-7) mol L(-1). The coupling of efficient quenching of quantum dot photoluminescence by quinone and the effective enzymatic reactions make this a simple and sensitive method for phenolic compound detection and great potential in the development of H2O2 biosensors for various analytes.

Competitive adsorption of furfural and phenolic compounds onto activated carbon in fixed bed column.

PubMed

Sulaymon, Abbas H; Ahmed, Kawther W

2008-01-15

For a multicomponent competitive adsorption of furfural and phenolic compounds, a mathematical model was builtto describe the mass transfer kinetics in a fixed bed column with activated carbon. The effects of competitive adsorption equilibrium constant, axial dispersion, external mass transfer, and intraparticle diffusion resistance on the breakthrough curve were studied for weakly adsorbed compound (furfural) and strongly adsorbed compounds (parachlorophenol and phenol). Experiments were carried out to remove the furfural and phenolic compound from aqueous solution. The equilibrium data and intraparticle diffusion coefficients obtained from separate experiments in a batch adsorber, by fitting the experimental data with theoretical model. The results show that the mathematical model includes external mass transfer and pore diffusion using nonlinear isotherms and provides a good description of the adsorption process for furfural and phenolic compounds in a fixed bed adsorber.

Anti-Amyloidogenic Properties of Some Phenolic Compounds

PubMed Central

Porzoor, Afsaneh; Alford, Benjamin; Hügel, Helmut M.; Grando, Danilla; Caine, Joanne; Macreadie, Ian

2015-01-01

A family of 21 polyphenolic compounds consisting of those found naturally in danshen and their analogues were synthesized and subsequently screened for their anti-amyloidogenic activity against the amyloid beta peptide (Aβ42) of Alzheimer’s disease. After 24 h incubation with Aβ42, five compounds reduced thioflavin T (ThT) fluorescence, indicative of their anti-amyloidogenic propensity (p < 0.001). TEM and immunoblotting analysis also showed that selected compounds were capable of hindering fibril formation even after prolonged incubations. These compounds were also capable of rescuing the yeast cells from toxic changes induced by the chemically synthesized Aβ42. In a second assay, a Saccharomyces cerevisiae AHP1 deletant strain transformed with GFP fused to Aβ42 was treated with these compounds and analyzed by flow cytometry. There was a significant reduction in the green fluorescence intensity associated with 14 compounds. We interpret this result to mean that the compounds had an anti-amyloid-aggregation propensity in the yeast and GFP-Aβ42 was removed by proteolysis. The position and not the number of hydroxyl groups on the aromatic ring was found to be the most important determinant for the anti-amyloidogenic properties. PMID:25898401

Isolation and identification of plant phenolic compounds in birch leaves: Air pollution stress and leaf phenolics

NASA Astrophysics Data System (ADS)

Loponen, Jyrki Mikael

Chromatographic (analytical and preparative HPLC), chemical (hydrolysis) and spectroscopic (UV, 1H NMR, 13C NMR and MS) techniques proved to be suitable tools for the structure identification of plant phenolic compounds. More than 30 individual phenolic compounds were detected and quantified. Detailed information of the structures of individual compounds was determined after isolation from birch leaves. Ten flavonoid glycosides were identified. Two of them, myricetin-3-O-α-L-(acetyl)-rhamnopyranoside and quercetin-3-O-α-L-(4/prime'-O-acetyl)- rhamnopyranoside, have been rarely found in birch leaves. Further, some characterized major phenolics with non- flavonoid structures in our study were 1-O-galloyl- β-D-(2-O-acetyl)-glucopyranose, gallic, chlorogenic, neochlorogenic, cis- and trans-forms of 3- and 5-p-coumaroylquinic acids. The presence of gallotannin group was evidenced by strong positive correlations between concentrations of these gallotannins (preliminary identified by HPLC and UV spectra) and the protein precipitation capacity of extracts. Content of gallotannins decreased with leaf growth and maturation. It is known that concentrations of phenolic compounds regularly increase in slowly growing stressed plants and therefore, it is natural that they are also sensitive to different forms of air pollution. Total content and the contents of some individual phenolics correlated negatively with the distance from the pollution source in our study area. In addition to comparing absolute concentrations of compounds in question, the within-tree correlations or within-tree variations of the relevant compounds between polluted and control areas were an alternative approach. Differences in pairwise correlations between the investigated leaf phenolic compounds indicated the competition between some gallotannins and p-coumaroylquinic acids on the polluted but not on the control site. Air pollution seems to be a stress factor for birch trees associated with accumulation, variability, as well as between-compound correlations of individual phenolics in leaves. Effects of atmospheric stress factors on phenolics with different structures result from the activation of the shikimate pathway.

Microwave-Assisted Drying for the Conservation of Honeybee Pollen.

PubMed

Canale, Angelo; Benelli, Giovanni; Castagna, Antonella; Sgherri, Cristina; Poli, Piera; Serra, Andrea; Mele, Marcello; Ranieri, Annamaria; Signorini, Francesca; Bientinesi, Matteo; Nicolella, Cristiano

2016-05-12

Bee pollen is becoming an important product thanks to its nutritional properties, including a high content of bioactive compounds such as essential amino acids, antioxidants, and vitamins. Fresh bee pollen has a high water content (15%-30% wt %), thus it is a good substrate for microorganisms. Traditional conservation methods include drying in a hot air chamber and/or freezing. These techniques may significantly affect the pollen organoleptic properties and its content of bioactive compounds. Here, a new conservation method, microwave drying, is introduced and investigated. The method implies irradiating the fresh pollen with microwaves under vacuum, in order to reduce the water content without reaching temperatures capable of thermally deteriorating important bioactive compounds. The method was evaluated by taking into account the nutritional properties after the treatment. The analyzed parameters were phenols, flavonoids, with special reference to rutin content, and amino acids. Results showed that microwave drying offers important advantages for the conservation of bee pollen. Irrespective of microwave power and treatment time, phenol and flavonoid content did not vary over untreated fresh pollen. Similarly, rutin content was unaffected by the microwave drying, suggesting that the microwave-assisted drying could be a powerful technology to preserve bioprotective compounds in fresh pollen.

Phenolic content and antioxidant and antimutagenic activities in tomato peel, seeds, and byproducts.

PubMed

Valdez-Morales, Maribel; Espinosa-Alonso, Laura Gabriela; Espinoza-Torres, Libia Citlali; Delgado-Vargas, Francisco; Medina-Godoy, Sergio

2014-06-11

The phenolic content and antioxidant and antimutagenic activities from the peel and seeds of different tomato types (grape, cherry, bola and saladette type), and simulated tomato industrial byproducts, were studied. Methanolic extracts were used to quantify total phenolic content, groups of phenolic compounds, antioxidant activities, and the profile of phenolic compounds (by HPLC-DAD). Antimutagenic activity was determined by Salmonella typhimurium assay. The total phenolic content and antioxidant activity of tomato and tomato byproducts were comparable or superior to those previously reported for whole fruit and tomato pomace. Phenolic compounds with important biological activities, such as caffeic acid, ferulic acid, chlorogenic acids, quercetin-3-β-O-glycoside, and quercetin, were quantified. Differences in all phenolic determinations due to tomato type and part of the fruit analyzed were observed, peel from grape type showing the best results. Positive antimutagenic results were observed in all samples. All evaluated materials could be used as a source of potential nutraceutical compounds.

Determination of the major phenolic compounds in pomegranate juices by HPLC−DAD−ESI-MS.

PubMed

Gómez-Caravaca, Ana María; Verardo, Vito; Toselli, Moreno; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto; Caboni, Maria Fiorenza

2013-06-05

Traditionally, pomegranate (Punica granatum L.) has been consumed as fresh fruit or as pomegranate juice. In this study, the main phenolic compounds of 12 pomegranate varieties and 5 pomegranate clones were determined by HPLC−DAD−ESI-MS. Two chromatographic methods with a fused-core C18 column and a classical HPLC system were developed. Thirteen anthocyanins and fourteen other phenolic compounds were determined in the pomegranate juices. As far as we are concerned, a new flavonol-glycoside, phellatin or its isomer amurensin, has been tentatively identified for the first time in pomegranate juices. Total phenolic content ranged from 580.8 to 2551.3 mg/L of pomegranate juice. Anthocyanins varied between 20 to 82% of total phenolic content. Flavonoids were 1.6-23.6% of total phenolic compounds, while phenolic acids and ellagitannins were in the range 16.4-65.8%. The five clones reported a phenolic content comparable with that of the other pomegranate samples.

Profiling of the Major Phenolic Compounds and Their Biosynthesis Genes in Sophora flavescens Aiton.

PubMed

Lee, Jeongyeo; Jung, Jaeeun; Son, Seung-Hyun; Kim, Hyun-Bi; Noh, Young-Hee; Min, Sung Ran; Park, Kun-Hyang; Kim, Dae-Soo; Park, Sang Un; Lee, Haeng-Soon; Kim, Cha Young; Kim, Hyun-Soon; Lee, Hyeong-Kyu; Kim, HyeRan

2018-01-01

Sophorae Radix ( Sophora flavescens Aiton) has long been used in traditional medicine in East Asia due to the various biological activities of its secondary metabolites. Endogenous contents of phenolic compounds (phenolic acid, flavonol, and isoflavone) and the main bioactive compounds of Sophorae Radix were analyzed based on the qualitative HPLC analysis and evaluated in different organs and at different developmental stages. In total, 11 compounds were detected, and the composition of the roots and aerial parts (leaves, stems, and flowers) was significantly different. trans-Cinnamic acid and p -coumaric acid were observed only in the aerial parts. Large amounts of rutin and maackiain were detected in the roots. Four phenolic acid compounds (benzoic acid, caffeic acid, ferulic acid, and chlorogenic acid) and four flavonol compounds (kaempferol, catechin hydrate, epicatechin, and rutin) were higher in aerial parts than in roots. To identify putative genes involved in phenolic compounds biosynthesis, a total of 41 transcripts were investigated. Expression patterns of these selected genes, as well as the multiple isoforms for the genes, varied by organ and developmental stage, implying that they are involved in the biosynthesis of various phenolic compounds both spatially and temporally.

Profiling of the Major Phenolic Compounds and Their Biosynthesis Genes in Sophora flavescens Aiton

PubMed Central

Son, Seung-Hyun; Kim, Hyun-Bi; Noh, Young-Hee; Min, Sung Ran; Park, Kun-Hyang; Kim, Dae-Soo; Lee, Haeng-Soon; Kim, Cha Young; Lee, Hyeong-Kyu

2018-01-01

Sophorae Radix (Sophora flavescens Aiton) has long been used in traditional medicine in East Asia due to the various biological activities of its secondary metabolites. Endogenous contents of phenolic compounds (phenolic acid, flavonol, and isoflavone) and the main bioactive compounds of Sophorae Radix were analyzed based on the qualitative HPLC analysis and evaluated in different organs and at different developmental stages. In total, 11 compounds were detected, and the composition of the roots and aerial parts (leaves, stems, and flowers) was significantly different. trans-Cinnamic acid and p-coumaric acid were observed only in the aerial parts. Large amounts of rutin and maackiain were detected in the roots. Four phenolic acid compounds (benzoic acid, caffeic acid, ferulic acid, and chlorogenic acid) and four flavonol compounds (kaempferol, catechin hydrate, epicatechin, and rutin) were higher in aerial parts than in roots. To identify putative genes involved in phenolic compounds biosynthesis, a total of 41 transcripts were investigated. Expression patterns of these selected genes, as well as the multiple isoforms for the genes, varied by organ and developmental stage, implying that they are involved in the biosynthesis of various phenolic compounds both spatially and temporally. PMID:29686587

Degradation of Phenolic Compounds and Ring Cleavage of Catechol by Phanerochaete chrysosporium

PubMed Central

Leatham, Gary F.; Crawford, R. L.; Kirk, T. Kent

1983-01-01

POL-88, a mutant of the white-rot fungus Phanerochaete chrysosporium, was selected for diminished phenol-oxidizing enzyme activity. A wide variety of phenolic compounds were degraded by ligninolytic cultures of this mutant. With several o-diphenolic substrates, degradation intermediates were produced that had UV spectra consistent with muconic acids. Extensive spectrophotometric and polarographic assays failed to detect classical ring-cleaving dioxygenases in cell homogenates or in extracts from ligninolytic cultures. Even so, a sensitive carrier-trapping assay showed that intact cultures degraded [U-14C]catechol to [14C]muconic acid, establishing the presence of a system capable of 1,2-intradiol fission. Significant accumulation of [14C]muconic acid into carrier occurred only when evolution of 14CO2 from [14C]catechol was inhibited by treating cultures with excess nutrient nitrogen (e.g., l-glutamic acid) or with cycloheximide. l-Glutamic acid is known from past work to repress the ligninolytic system in P. chrysosporium and to mimic the effect of cycloheximide. The results here indicate, therefore, that the enzyme system responsible for degrading ring-cleavage products to CO2 turns over faster than does the system responsible for ring cleavage. PMID:16346340

Bioactive components from flowers of Sambucus nigra L. increase glucose uptake in primary porcine myotube cultures and reduce fat accumulation in Caenorhabditis elegans.

PubMed

Bhattacharya, Sumangala; Christensen, Kathrine B; Olsen, Louise C B; Christensen, Lars P; Grevsen, Kai; Færgeman, Nils J; Kristiansen, Karsten; Young, Jette F; Oksbjerg, Niels

2013-11-20

Obesity and insulin resistance in skeletal muscles are major features of type 2 diabetes. In the present study, we examined the potential of Sambucus nigra flower (elderflowers) extracts to stimulate glucose uptake (GU) in primary porcine myotubes and reduce fat accumulation (FAc) in Caenorhabditis elegans. Bioassay guided chromatographic fractionations of extracts and fractions resulted in the identification of naringenin and 5-O- caffeoylquinic acid exhibiting a significant increase in GU. In addition, phenolic compounds related to those found in elderflowers were also tested, and among these, kaempferol, ferulic acid, p-coumaric acid, and caffeic acid increased GU significantly. FAc was significantly reduced in C. elegans, when treated with elderflower extracts, their fractions and the metabolites naringenin, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, quercetin-3-O-5″-acetylglycoside, kaempferol-3-O-rutinoside, isorhamnetin-3-O-rutinoside, and isorhamnetin-3-O-glucoside and the related phenolic compounds kaempferol and ferulic acid. The study indicates that elderflower extracts contain bioactive compounds capable of modulating glucose and lipid metabolism, suitable for nutraceutical and pharmaceutical applications.

Breads enriched with guava flour as a tool for studying the incorporation of phenolic compounds in bread melanoidins.

PubMed

Alves, Genilton; Perrone, Daniel

2015-10-15

In the present study we aimed at studying, for the first time, the incorporation of phenolic compounds into bread melanoidins. Fermentation significantly affected the phenolics profile of bread doughs. Melanoidins contents continuously increased from 24.1 mg/g to 71.9 mg/g during baking, but their molecular weight decreased at the beginning of the process and increased thereafter. Enrichment of white wheat bread with guava flour increased the incorporation of phenolic compounds up to 2.4-fold. Most phenolic compounds showed higher incorporation than release rates during baking, leading to increases from 3.3- to 13.3-fold in total melanoidin-bound phenolics. Incorporation patterns suggested that phenolic hydroxyls, but not glycosidic bonds of melanoidin-bound phenolics are cleaved during thermal processing. Antioxidant capacity of bread melanoidins increased due to enrichment with guava flour and increasing baking periods and was partially attributed to bound phenolics. Moreover, FRAP assay was more sensitive to measure this parameter than TEAC assay. Copyright © 2015 Elsevier Ltd. All rights reserved.

Degradation of Malaysian peatlands decreases levels of phenolics in soil and in leaves of Macaranga pruinosa

NASA Astrophysics Data System (ADS)

Yule, Catherine; Lim, Yau; Lim, Tse

2016-04-01

Indo-Malaysian tropical peat swamp forests (PSF) sequester enormous stores of carbon in the form of phenolic compounds, particularly lignin as well as tannins. These phenolic compounds are crucial for ecosystem functioning in PSF through their inter-related roles in peat formation and plant defenses. Disturbance of PSF causes destruction of the peat substrate, but the specific impact of disturbance on phenolic compounds in peat and its associated vegetation has not previously been examined. A scale was developed to score peatland degradation based on the three major human impacts that affect tropical PSF - logging, drainage and fire. The objectives of this study were to compare the amount of phenolic compounds in Macaranga pruinosa, a common PSF tree, and in the peat substrate along a gradient of peatland degradation from pristine peat swamp forest to cleared, drained and burnt peatlands. We examined phenolic compounds in M. pruinosa and in peat and found that levels of total phenolic compounds and total tannins decrease in the leaves of M.pruinosa and also in the surface peat layers with an increase in peatland degradation. We conclude that waterlogged conditions preserve the concentration of phenolic compounds in peat, and that even PSF that has been previously logged but which has recovered a full canopy cover will have high levels of total phenolic content (TPC) in peat. High levels of TPC in peat and in the flora are vital for the inhibition of decomposition of organic matter and this is crucial for the accretion of peat and the sequestration of carbon. Thus regional PSF flourish despite the phenolic rich, toxic, waterlogged, nutrient poor, conditions, and reversal of such conditions is a sign of degradation.

Phenolic compounds and fatty acid composition of organic and conventional grown pecan kernels

USDA-ARS?s Scientific Manuscript database

In this study, differences in contents of phenolic compounds and fatty acids in pecan kernels of organically versus conventionally grown pecan cultivars (‘Desirable’, ‘Cheyenne’, and ‘Wichita’) were evaluated. Although we were able to identify nine phenolic compounds (gallic acid, catechol, catechin...

Cross-reactivity of antibodies with phenolic compounds in pistachios during quantification of ochratoxin A by commercial enzyme-linked immunosorbent assay kits.

PubMed

Lee, Hyun Jung; Meldrum, Alexander D; Rivera, Nicholas; Ryu, Dojin

2014-10-01

Ochratoxin A (OTA), a nephrotoxic mycotoxin, naturally occurs in wide range of agricultural commodities. Typical screening of OTA involves various enzyme-linked immunosorbent assay (ELISA) methods. Pistachio (Pistacia vera L.) is a rich source of phenolic compounds that may result in a false positive due to structural similarities to OTA. The present study investigated the cross-reactivity profiles of phenolic compounds using two commercial ELISA test kits. High-performance liquid chromatography was used to confirm the concentration of OTA in the pistachio samples and compared with the results obtained from ELISA. When the degree of interaction and 50 % inhibitory concentration of phenolic compounds were determined, the cross-reactivity showed a pattern similar to that observed with the commercial ELSIA kits, although quantitatively different. In addition, the degree of interaction increased with the increasing concentration of phenolic compounds. The ELISA value had stronger correlations with the content of total phenolic compound, gallic acid, and catechin (R(2) = 0.757, 0.732, and 0.729, respectively) compared with epicatechin (R(2) = 0.590). These results suggest that phenolic compounds in pistachio skins may cross-react with the OTA antibody and lead to a false positive or to an overestimation of OTA concentration in ELISA-based tests.

Phytochemical Compounds and Antioxidant Capacity of Tucum-Do-Cerrado (Bactris setosa Mart), Brazil's Native Fruit.

PubMed

Rosa, Fernanda R; Arruda, Andréa F; Siqueira, Egle M A; Arruda, Sandra F

2016-02-23

This study identified major phenolic compounds of the tucum-do-cerrado (Bactris setosa) peel, as well as antioxidant activity and total phytochemical compound concentration of different extracts of the peel and pulp of this fruit. Phenolic compounds of the different extracts of tucum-do-cerrado peel were identified and quantified using a high-performance liquid chromatography system coupled to a diode array detector (DAD). Total phytochemical compound content was determined by spectrophotometric assays and the antioxidant activity by ferric reducing antioxidant power and β-carotene/linoleic assays. Total phenolic, flavanols, total anthocyanins and yellow flavonoids concentration of tucum-do-cerrado were 122-, 14-, 264- and 61-fold higher in the peel than in the pulp, respectively. The aqueous, methanolic and ethanolic extracts of the tucum-do-cerrado peel exhibited higher antioxidant activity compared to its pulp. Flavanols, anthocyanins, flavones, phenolic acids and stilbenes were the main phenolic classes identified in the tucum-do-cerrado peel extracts. Results suggest that the antioxidant capacity and the phytochemical compound content of the tucum-do-cerrado are mainly associated with the peel. Although flavonoids are the main compounds identified in tucum-do-cerrado peel, other phenolics identified in minor amounts, such as phenolic acids and stilbenes, may be responsible for the high antioxidant capacity of the fruit.

Effect of cadmium on phenolic compounds, antioxidant enzyme activity and oxidative stress in blueberry (Vaccinium corymbosum L.) plantlets grown in vitro.

PubMed

Manquián-Cerda, K; Escudey, M; Zúñiga, G; Arancibia-Miranda, N; Molina, M; Cruces, E

2016-11-01

Cadmium (Cd(2+)) can affect plant growth due to its mobility and toxicity. We evaluated the effects of Cd(2+) on the production of phenolic compounds and antioxidant response of Vaccinium corymbosum L. Plantlets were exposed to Cd(2+) at 50 and 100µM for 7, 14 and 21 days. Accumulation of malondialdehyde (MDA), hydrogen peroxide (H2O2) and the antioxidant enzyme SOD was determined. The profile of phenolic compounds was evaluated using LC-MS. The antioxidant activity was measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the ferric reducing antioxidant power test (FRAP). Cd(2+) increased the content of MDA, with the highest increase at 14 days. The presence of Cd(2+) resulted in changes in phenolic compounds. The main phenolic compound found in blueberry plantlets was chlorogenic acid, whose abundance increased with the addition of Cd(2+) to the medium. The changes in the composition of phenolic compounds showed a positive correlation with the antioxidant activity measured using FRAP. Our results suggest that blueberry plantlets produced phenolic compounds with reducing capacity as a selective mechanism triggered by the highest activity of Cd(2+). Copyright © 2016 Elsevier Inc. All rights reserved.

Phytochemical Compounds and Antioxidant Capacity of Tucum-Do-Cerrado (Bactris setosa Mart), Brazil’s Native Fruit

PubMed Central

Rosa, Fernanda R.; Arruda, Andréa F.; Siqueira, Egle M. A.; Arruda, Sandra F.

2016-01-01

This study identified major phenolic compounds of the tucum-do-cerrado (Bactris setosa) peel, as well as antioxidant activity and total phytochemical compound concentration of different extracts of the peel and pulp of this fruit. Phenolic compounds of the different extracts of tucum-do-cerrado peel were identified and quantified using a high-performance liquid chromatography system coupled to a diode array detector (DAD). Total phytochemical compound content was determined by spectrophotometric assays and the antioxidant activity by ferric reducing antioxidant power and β-carotene/linoleic assays. Total phenolic, flavanols, total anthocyanins and yellow flavonoids concentration of tucum-do-cerrado were 122-, 14-, 264- and 61-fold higher in the peel than in the pulp, respectively. The aqueous, methanolic and ethanolic extracts of the tucum-do-cerrado peel exhibited higher antioxidant activity compared to its pulp. Flavanols, anthocyanins, flavones, phenolic acids and stilbenes were the main phenolic classes identified in the tucum-do-cerrado peel extracts. Results suggest that the antioxidant capacity and the phytochemical compound content of the tucum-do-cerrado are mainly associated with the peel. Although flavonoids are the main compounds identified in tucum-do-cerrado peel, other phenolics identified in minor amounts, such as phenolic acids and stilbenes, may be responsible for the high antioxidant capacity of the fruit. PMID:26907338

Simultaneous determination of phenolic compounds in Cynthiana grape (Vitis aestivalis) by high performance liquid chromatography-electrospray ionisation-mass spectrometry.

PubMed

Ramirez-Lopez, L M; McGlynn, W; Goad, C L; Mireles Dewitt, C A

2014-04-15

Phenolic acids, flavanols, flavonols and stilbenes (PAFFS) were isolated from whole grapes, juice, or pomace and purified using enzymatic hydrolysis. Only anthocyanin mono-glucosides and a few of the oligomers from Cynthiana grape (Vitis aestivalis) were analysed. Flavonoid-anthocyanin mono-glucosides (FA) were isolated using methanol/0.1% hydrochloric acid extraction. In addition, crude extractions of phenolic compounds from Cynthiana grape using 50% methanol, 70% methanol, 50% acetone, 0.01% pectinase, or petroleum ether were also evaluated. Reverse phase high performance liquid chromatography (RP-HPLC) with photodiode array (PDA) detector was used to identify phenolic compounds. A method was developed for simultaneous separation, identification and quantification of both PAFFS and FA. Quantification was performed by the internal standard method using a five points regression graph of the UV-visible absorption data collected at the wavelength of maximum absorbance for each analyte. From whole grape samples nine phenolic compounds were tentatively identified and quantified. The individual phenolic compounds content varied from 3 to 875 mg kg⁻¹ dry weight. For juice, twelve phenolic compounds were identified and quantified. The content varied from 0.07 to 910 mg kg⁻¹ dry weight. For pomace, a total of fifteen phenolic compounds were tentatively identified and quantified. The content varied from 2 mg kg⁻¹ to 198 mg kg⁻¹ dry matter. Results from HPLC analysis of the samples showed that gallic acid and (+)-catechin hydrate were the major phenolic compounds in both whole grapes and pomace. Cyanidin and petunidin 3-O-glucoside were the major anthocyanin glucosides in the juice. Published by Elsevier Ltd.

Characterization and quantification of phenolic compounds in four tomato (Lycopersicon esculentum L.) farmers' varieties in northeastern Portugal homegardens.

PubMed

Barros, Lillian; Dueñas, Montserrat; Pinela, José; Carvalho, Ana Maria; Buelga, Celestino Santos; Ferreira, Isabel C F R

2012-09-01

Tomato (Lycopersicon esculentum L.) is one of the most widely consumed fresh and processed vegetables in the world, and contains bioactive key components. Phenolic compounds are one of those components and, according to the present study, farmers' varieties of tomato cultivated in homegardens from the northeastern Portuguese region are a source of phenolic compounds, mainly phenolic acid derivatives. Using HPLC-DAD-ESI/MS, it was concluded that a cis p-coumaric acid derivative was the most abundant compound in yellow (Amarelo) and round (Batateiro) tomato varieties, while 4-O-caffeolyquinic acid was the most abundant in long (Comprido) and heart (Coração) varieties. The most abundant flavonoid was quercetin pentosylrutinoside in the four tomato varieties. Yellow tomato presented the highest levels of phenolic compounds (54.23 μg/g fw), including phenolic acids (43.30 μg/g fw) and flavonoids (10.93 μg/g fw). The phenolic compounds profile obtained for the studied varieties is different from other tomato varieties available in different countries, which is certainly related to genetic features, cultivation conditions, and handling and storage methods associated to each sample.

Variability of Virgin Olive Oil Phenolic Compounds in a Segregating Progeny from a Single Cross in Olea europaea L. and Sensory and Nutritional Quality Implications

PubMed Central

Pérez, Ana G.; León, Lorenzo; Pascual, Mar; Romero-Segura, Carmen; Sánchez-Ortiz, Araceli; de la Rosa, Raúl; Sanz, Carlos

2014-01-01

Virgin olive oil phenolic compounds are responsible for its nutritional and sensory quality. The synthesis of phenolic compounds occurs when enzymes and substrates meet as olive fruit is crushed during the industrial process to obtain the oil. The genetic variability of the major phenolic compounds of virgin olive oil was studied in a progeny of the cross of Picual x Arbequina olive cultivars (Olea europaea L.). They belong to four different groups: compounds that included tyrosol or hydroxytyrosol in their molecules, lignans, flavonoids, and phenolic acids. Data of phenolics in the oils showed that the progeny displayed a large degree of variability, widely transgressing the genitor levels. This high variability can be of interest on breeding programs. Thus, multivariate analysis allowed to identify genotypes within the progeny particularly interesting in terms of phenolic composition and deduced organoleptic and nutritional quality. The present study has demonstrated that it is possible to obtain enough degree of variability with a single cross of olive cultivars for compounds related to the nutritional and organoleptic properties of virgin olive oil. PMID:24651694

Variability of virgin olive oil phenolic compounds in a segregating progeny from a single cross in Olea europaea L. and sensory and nutritional quality implications.

PubMed

Pérez, Ana G; León, Lorenzo; Pascual, Mar; Romero-Segura, Carmen; Sánchez-Ortiz, Araceli; de la Rosa, Raúl; Sanz, Carlos

2014-01-01

Virgin olive oil phenolic compounds are responsible for its nutritional and sensory quality. The synthesis of phenolic compounds occurs when enzymes and substrates meet as olive fruit is crushed during the industrial process to obtain the oil. The genetic variability of the major phenolic compounds of virgin olive oil was studied in a progeny of the cross of Picual x Arbequina olive cultivars (Olea europaea L.). They belong to four different groups: compounds that included tyrosol or hydroxytyrosol in their molecules, lignans, flavonoids, and phenolic acids. Data of phenolics in the oils showed that the progeny displayed a large degree of variability, widely transgressing the genitor levels. This high variability can be of interest on breeding programs. Thus, multivariate analysis allowed to identify genotypes within the progeny particularly interesting in terms of phenolic composition and deduced organoleptic and nutritional quality. The present study has demonstrated that it is possible to obtain enough degree of variability with a single cross of olive cultivars for compounds related to the nutritional and organoleptic properties of virgin olive oil.

Analysis of eleven phenolic compounds including novel p-coumaroyl derivatives in lettuce (Lactuca sativa L.) by ultra-high-performance liquid chromatography with photodiode array and mass spectrometry detection.

PubMed

Ribas-Agustí, Albert; Gratacós-Cubarsí, Marta; Sárraga, Carmen; García-Regueiro, José-Antonio; Castellari, Massimo

2011-01-01

Lettuce is a widely consumed vegetable and a good source of phenolic compounds. Several factors (genetic, agronomical and environmental) can influence the lettuce composition; their effects are not completely defined and more studies are needed on this topic. To develop an improved ultra-high-performance liquid chromatography (UHPLC) method to quantify the main target intact phenolic compounds in lettuce. UHPLC identification of the compounds was supported by PAD spectra and MS(n) analyses. Quantification was carried out by PAD, by creating matrix-matched calibration curves at the specific wavelength for each compound. Sample pretreatment was simplified, with neither purification nor hydrolysis steps. Chromatographic conditions were chosen to minimise matrix interferences and to give a suitable separation of the major phenolic compounds within 27 min. The method allowed the quantification of 11 intact phenolic compounds in Romaine lettuces, including phenolic acids (caffeoyl and p-coumaroyl esters) and flavonoids (quercetin glycosides). Four p-coumaroyl esters were tentatively identified and quantified for the first time in lettuce. The main intact phenolic compounds, including four novel p-coumaroyl esters, were simultaneously quantified in lettuce with optimal performances and a reduced total time of analysis. These findings make headway in the understanding of the lettuce phytochemicals with potential nutritional relevance. Copyright © 2011 John Wiley & Sons, Ltd.

Alzheimer's-associated A{beta} oligomers show altered structure, immunoreactivity and synaptotoxicity with low doses of oleocanthal

DOE Office of Scientific and Technical Information (OSTI.GOV)

Pitt, Jason; Roth, William; Lacor, Pascale

2009-10-15

It now appears likely that soluble oligomers of amyloid-{beta}{sub 1-42} peptide, rather than insoluble fibrils, act as the primary neurotoxin in Alzheimer's disease (AD). Consequently, compounds capable of altering the assembly state of these oligomers (referred to as ADDLs) may have potential for AD therapeutics. Phenolic compounds are of particular interest for their ability to disrupt A{beta} oligomerization and reduce pathogenicity. This study has focused on oleocanthal (OC), a naturally-occurring phenolic compound found in extra-virgin olive oil. OC increased the immunoreactivity of soluble A{beta} species, when assayed with both sequence- and conformation-specific A{beta} antibodies, indicating changes in oligomer structure. Analysismore » of oligomers in the presence of OC showed an upward shift in MW and a ladder-like distribution of SDS-stable ADDL subspecies. In comparison with control ADDLs, oligomers formed in the presence of OC (A{beta}-OC) showed equivalent colocalization at synapses but exhibited greater immunofluorescence as a result of increased antibody recognition. The enhanced signal at synapses was not due to increased synaptic binding, as direct detection of fluorescently-labeled ADDLs showed an overall reduction in ADDL signal in the presence of OC. Decreased binding to synapses was accompanied by significantly less synaptic deterioration assayed by drebrin loss. Additionally, treatment with OC improved antibody clearance of ADDLs. These results indicate oleocanthal is capable of altering the oligomerization state of ADDLs while protecting neurons from the synaptopathological effects of ADDLs and suggest OC as a lead compound for development in AD therapeutics.« less

Influence of Protein-Phenolic Complex on the Antioxidant Capacity of Flaxseed (Linum usitatissimum L.) Products.

PubMed

Guimarães Drummond E Silva, Fernanda; Miralles, Beatriz; Hernández-Ledesma, Blanca; Amigo, Lourdes; Iglesias, Amadeu Hoshi; Reyes Reyes, Felix Guillermo; Netto, Flavia Maria

2017-02-01

The impact of the naturally present phenolic compounds and/or proteins on the antioxidant capacity of flaxseed products (phenolic fraction, protein concentrates, and hydrolysates) before and after simulated gastrointestinal digestion was studied. For that, whole and phenolic reduced products were assessed. Four glycosylated phenolic compounds (secoisolariciresinol and ferulic, p-coumaric, and caffeic acids) were identified in flaxseed products. Phenolic fraction exerts the highest antioxidant capacity that increased by alkaline hydrolysis and by simulated gastrointestinal digestion. The action of Alcalase and digestive enzymes resulted in an increase of the antioxidant capacity of whole and phenolic reduced products. Principal component analysis showed that proteinaceous samples act as antioxidant is by H + transfer, while those samples containing phenolic compounds exert their effects by both electron donation and H + transfer mechanisms. Protein/peptide-phenolic complexation, confirmed by fluorescence spectra, exerted a positive effect on the antioxidant capacity, mainly in protein concentrates.

Potentiation of the bioavailability of blueberry phenolic compounds by co-ingested grape phenolic compounds in mice, revealed by targeted metabolomic profiling in plasma and feces.

PubMed

Dudonné, Stéphanie; Dal-Pan, Alexandre; Dubé, Pascal; Varin, Thibault V; Calon, Frédéric; Desjardins, Yves

2016-08-10

The low bioavailability of dietary phenolic compounds, resulting from poor absorption and high rates of metabolism and excretion, is a concern as it can limit their potential beneficial effects on health. Targeted metabolomic profiling in plasma and feces of mice supplemented for 15 days with a blueberry extract, a grape extract or their combination revealed significantly increased plasma concentrations (3-5 fold) of blueberry phenolic metabolites in the presence of a co-ingested grape extract, associated with an equivalent decrease in their appearance in feces. Additionally, the repeated daily administration of the blueberry-grape combination significantly increased plasma phenolic concentrations (2-3-fold) compared to animals receiving only a single acute dose, with no such increase being observed with individual extracts. These findings highlight a positive interaction between blueberry and grape constituents, in which the grape extract enhanced the absorption of blueberry phenolic compounds. This study provides for the first time in vivo evidence of such an interaction occurring between co-ingested phenolic compounds from fruit extracts leading to their improved bioavailability.

Changes in phenolic compounds and their antioxidant capacities in jujube (Ziziphus jujuba Miller) during three edible maturity stages

USDA-ARS?s Scientific Manuscript database

This study investigated the changes in total phenolic content (TPC), total flavonoid content (TFC), individual phenolic compound content, DPPH radical scavenging activity and antioxidant capacity measured by FRAP assay of four phenolic fractions (free, esterified, glycosided and insoluble-bound) fro...

Reaction of formaldehyde with phenols: a computational chemistry study.

Treesearch

Tohru Mitsunaga; Anthony H. Conner; Charles G. Hill

2001-01-01

Phenolic resins are important adhesives used by the forest products industry. The phenolic compounds in these resins are derived primarily from petrochemical sources. Alternate sources of phenolic compounds include tannins, lignins, biomass pyrolysis products, and coal gasification products. Because of variations in their chemical structures, the reactivities of these...

Virgin olive oil rich in phenolic compounds modulates the expression of atherosclerosis-related genes in vascular endothelium.

PubMed

Meza-Miranda, Eliana R; Rangel-Zúñiga, Oriol A; Marín, Carmen; Pérez-Martínez, Pablo; Delgado-Lista, Javier; Haro, Carmen; Peña-Orihuela, Patricia; Jiménez-Morales, Ana I; Malagón, María M; Tinahones, Francisco J; López-Miranda, José; Pérez-Jiménez, Francisco; Camargo, Antonio

2016-03-01

Previous studies have shown the anti-inflammatory and antioxidant properties of phenolic compounds of virgin olive oil (VOO). However, the effect of bioavailable phenolic compounds on the vascular endothelium is unknown. We aimed to evaluate the effect of the consumption of virgin olive oil rich in phenolic compounds on the vascular endothelium. We treated HUVEC with human serum obtained in fasting state and after the intake of a breakfast prepared with VOO with a high or low content of phenolic compounds. Treatment of HUVEC with serum obtained 2 h after the intake of the high-phenol VOO-based breakfast decreased p65 and MCP-1 gene expression (p < 0.001 and p = 0.002, respectively) and increased MT-CYB, SDHA and SOD1 gene expression (p = 0.004, p = 0.012 and p = 0.001, respectively), as compared with the treatment of HUVEC with the serum obtained 2 h after the intake of the low-phenol VOO-based breakfast. The treatment with serum obtained 4 h after the intake of the high-phenol VOO-based breakfast decreased MCP-1 and CAT gene expression (p < 0.001 and p = 0.003, respectively) and increased MT-CYB gene expression (p < 0.001), as compared to the treatment with serum obtained 4 h after the intake of the low-phenol VOO-based breakfast. Our results suggest that the consumption of virgin olive oil rich in phenolic compounds may reduce the risk of atherosclerosis development by decreasing inflammation and improving the antioxidant profile in the vascular endothelium.

UV-C and hyperoxia abiotic stresses to improve healthiness of carrots: study of combined effects.

PubMed

Formica-Oliveira, Anna Carolina; Martínez-Hernández, Ginés Benito; Aguayo, Encarna; Gómez, Perla A; Artés, Francisco; Artés-Hernández, Francisco

2016-09-01

Phenolic compounds are phytochemicals with high health-promoting properties. Carrot is a vegetable highly worldwide consumed although its phenolic content is low compared to other plant products. The aim of this work was to evaluate changes in phenolic compounds in carrots caused by abiotic stresses. The phenylalanine ammonia-lyase (PAL) activity, phenolic compounds and total antioxidant capacity (TAC) changes during storage up to 72 h at 15 °C after wounding (shredding), 9 kJ UV-C m -2 pretreatment and hyperoxia (80 kPa) conditions of carrots were studied. Shredding and hyperoxia storage induced the highest phenolic compounds and TAC enhancements. Accumulation of phenolic compounds in shredded carrots could be structured in the following phases: 1st phase (<24 h): unchanged phenolic compounds levels with minimum PAL activity; 2nd phase (24-48 h): moderate phenolic increases (≈600-700 mg CAE kg -1 accumulated in 24 h) concurring with the greatest increase of PAL activity; 3nd phase (48-72 h): high phenolic increases (≈1600-2700 mg CAE kg -1 , accumulated in 24 h) while a moderate increment of PAL activity was registered. Although UV-C pretreatment of shreds reduced phenolic accumulation, 600 % increments were still registered in those samples stored under hyperoxia conditions for 72 h. However, the contents of chlorogenic acid at 72 h were 1.4-fold higher in irradiated shreds under hyperoxia compared to the same samples under air conditions.

Metabolism of 4-Chloro-2-Methylphenoxyacetic Acid by Soil Bacteria

PubMed Central

Bollag, J.-M.; Helling, C. S.; Alexander, M.

1967-01-01

A microorganism capable of degrading 4-chloro-2-methylphenoxyacetic acid (MCPA) was isolated from soil and identified as Flavobacterium peregrinum. All of the chlorine of MCPA was released as chloride, and the carboxyl-carbon was converted to volatile products by growing cultures of the bacterium, but a phenol accumulated in the medium. The phenol was identified as 4-chloro-2-methylphenol on the basis of its gas chromatographic and infrared characteristics. Extracts of cells of F. peregrinum and of a phenoxyacetate-metabolizing Arthrobacter sp. dehalogenated MCPA and several catechols but not 4-chloro-2-methylanisole. The Arthrobacter sp. cell extract was fractionated, and an enzyme preparation was obtained which catalyzed the conversion of MCPA to 4-chloro-2-methylphenol. The latter compound was not metabolized unless reduced nicotinamide adenine dinucleotide phosphate was added to the fractionated extract. The phenol in turn was apparently oxidized to a catechol by components of the enzyme preparation. PMID:16349751

Effect of Steam Blanching and Drying on Phenolic Compounds of Litchi Pericarp.

PubMed

Kessy, Honest N E; Hu, Zhuoyan; Zhao, Lei; Zhou, Molin

2016-06-03

The effects of different treatment methods on the stability and antioxidant capacity of the bioactive phenolic compounds of litchi pericarps were investigated. Fresh litchi pericarps were open air-dried, steam-blanched for 3 min in combination with hot air oven drying at 60 and 80 °C, and unblanched pericarps were dried in a hot air oven at 40, 60, 70 and 80 °C until equilibrium weight was reached. The total phenolic compounds, flavonoids, anthocyanins, proanthocyanidins and individual procyanidins, and antioxidant activity were analyzed. The combination of blanching and drying at 60 °C significantly (p < 0.05) improved the release of phenolic compounds, individual procyanidins, and the extracts' antioxidant capacity compared with the unblanched hot air oven-dried and open air-dried pericarps. Drying of fresh unblanched litchi pericarps in either open air or a hot air oven caused significant losses (p < 0.05) in phenolic compounds and individual procyanidins, leading to a reduction in the antioxidant activity. A similar increase, retention or reduction was reflected in flavonoids, proanthocyanidins and anthocyanins because they are sub-groups of phenolic compounds. Ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging capacity of the treated pericarps were significantly correlated (r ≥ 0.927, p < 0.01) with the total phenolic compounds. Thus, the combination of steam blanching and drying treatments of fresh litchi pericarps could produce a stable and dry litchi pericarp that maintains phenolic compounds and antioxidant capacity as a raw material for further recovery of the phytochemicals.

Phenolic profiles and antioxidant activity of Turkish Tombul hazelnut samples (natural, roasted, and roasted hazelnut skin).

PubMed

Pelvan, Ebru; Olgun, Elmas Öktem; Karadağ, Ayşe; Alasalvar, Cesarettin

2018-04-01

The phenolic profiles and antioxidant status of hazelnut samples [natural (raw) hazelnut, roasted hazelnut, and roasted hazelnut skin] were compared. Free and bound (ester-linked and glycoside-linked) phenolic acids were examined using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Comprehensive identification of phenolics was carried out using Q-exactive hybrid quadrupole-orbitrap mass spectrometer (Q-OT-MS). Samples were also assessed for their total phenolics and antioxidant activities using three different assays. Ten free and bound phenolic acids were quantified in hazelnut samples. Roasted hazelnut skin contained the highest content of total phenolic acids, followed by natural and roasted hazelnuts. The majority of phenolic acids were present in the bound form. Using a Q-OT-MS, 22 compounds were tentatively identified, 16 of which were identified for the first time in hazelnut samples. The newly identified compounds consisted of flavonoids, phenolic acids and related compounds, hydrolysable tannins and related compounds, and other phenolics. Three antioxidant assays demonstrated similar trends that roasted hazelnut skin rendered the highest activity. The present work suggests that roasted hazelnut skin is a rich source of phenolics and can be considered as a value-added co-product for use as functional food ingredient and antioxidant. Copyright © 2017 Elsevier Ltd. All rights reserved.

Changes in polyphenol and sugar concentrations in wild type and genetically modified Nicotiana langsdorffii Weinmann in response to water and heat stress.

PubMed

Ancillotti, Claudia; Bogani, Patrizia; Biricolti, Stefano; Calistri, Elisa; Checchini, Leonardo; Ciofi, Lorenzo; Gonnelli, Cristina; Del Bubba, Massimo

2015-12-01

In this study wild type Nicotiana langsdorffii plants were genetically transformed by the insertion of the rat gene (gr) encoding the glucocorticoid receptor or the rolC gene and exposed to water and heat stress. Water stress was induced for 15 days by adding 20% PEG 6000 in the growth medium, whereas the heat treatment was performed at 50 °C for 2 h, after that a re-growing capability study was carried out. The plant response to stress was investigated by determining electrolyte leakage, dry weight biomass production and water content. These data were evaluated in relation to antiradical activity and concentrations of total polyphenols, selected phenolic compounds and some soluble sugars, as biochemical indicators of metabolic changes due to gene insertion and/or stress treatments. As regards the water stress, the measured physiological parameters evidenced an increasing stress level in the order rolC < gr < WT plants (e.g. about 100% and 50% electrolyte leakage increase in WT and gr samples, respectively) and complied with the biochemical pattern, which consisted in a general decrease of antiradical activity and phenolics, together with an increase in sugars. As regard heat stress, electrolyte leakage data were only in partial agreement with the re-growing capability study. In fact, according to this latter evaluation, gr was the genotype less affected by the heat shock. In this regard, sugars and especially phenolic compounds are informative of the long-term effects due to heat shock treatment. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Influence of phenolic compounds on the growth and arginine deiminase system in a wine lactic acid bacterium

PubMed Central

Alberto, María R.; de Nadra, María C. Manca; Arena, Mario E.

2012-01-01

The influence of seven phenolic compounds, normally present in wine, on the growth and arginine deiminase system (ADI) of Lactobacillus hilgardii X1B, a wine lactic acid bacterium, was established. This system provides energy for bacterial growth and produces citrulline that reacts with ethanol forming the carcinogen ethyl carbamate (EC), found in some wines. The influence of phenolic compounds on bacterial growth was compound dependent. Growth and final pH values increased in presence of arginine. Arginine consumption decreased in presence of protocatechuic and gallic acids (31 and 17%, respectively) and increased in presence of quercetin, rutin, catechin and the caffeic and vanillic phenolic acids (between 10 and 13%, respectively). ADI enzyme activities varied in presence of phenolic compounds. Rutin, quercetin and caffeic and vanillic acids stimulated the enzyme arginine deiminase about 37–40%. Amounts of 200 mg/L gallic and protocatechuic acids inhibited the arginine deiminase enzyme between 53 and 100%, respectively. Ornithine transcarbamylase activity was not modified at all concentrations of phenolic compounds. As gallic and protocatechuic acids inhibited the arginine deiminase enzyme that produces citrulline, precursor of EC, these results are important considering the formation of toxic compounds. PMID:24031815

The Potential of Plant Phenolics in Prevention and Therapy of Skin Disorders

PubMed Central

Działo, Magdalena; Mierziak, Justyna; Korzun, Urszula; Preisner, Marta; Szopa, Jan; Kulma, Anna

2016-01-01

Phenolic compounds constitute a group of secondary metabolites which have important functions in plants. Besides the beneficial effects on the plant host, phenolic metabolites (polyphenols) exhibit a series of biological properties that influence the human in a health-promoting manner. Evidence suggests that people can benefit from plant phenolics obtained either by the diet or through skin application, because they can alleviate symptoms and inhibit the development of various skin disorders. Due to their natural origin and low toxicity, phenolic compounds are a promising tool in eliminating the causes and effects of skin aging, skin diseases, and skin damage, including wounds and burns. Polyphenols also act protectively and help prevent or attenuate the progression of certain skin disorders, both embarrassing minor problems (e.g., wrinkles, acne) or serious, potentially life-threatening diseases such as cancer. This paper reviews the latest reports on the potential therapy of skin disorders through treatment with phenolic compounds, considering mostly a single specific compound or a combination of compounds in a plant extract. PMID:26901191

The Potential of Plant Phenolics in Prevention and Therapy of Skin Disorders.

PubMed

Działo, Magdalena; Mierziak, Justyna; Korzun, Urszula; Preisner, Marta; Szopa, Jan; Kulma, Anna

2016-02-18

Phenolic compounds constitute a group of secondary metabolites which have important functions in plants. Besides the beneficial effects on the plant host, phenolic metabolites (polyphenols) exhibit a series of biological properties that influence the human in a health-promoting manner. Evidence suggests that people can benefit from plant phenolics obtained either by the diet or through skin application, because they can alleviate symptoms and inhibit the development of various skin disorders. Due to their natural origin and low toxicity, phenolic compounds are a promising tool in eliminating the causes and effects of skin aging, skin diseases, and skin damage, including wounds and burns. Polyphenols also act protectively and help prevent or attenuate the progression of certain skin disorders, both embarrassing minor problems (e.g., wrinkles, acne) or serious, potentially life-threatening diseases such as cancer. This paper reviews the latest reports on the potential therapy of skin disorders through treatment with phenolic compounds, considering mostly a single specific compound or a combination of compounds in a plant extract.

Phenolic root exudate and tissue compounds vary widely among temperate forest tree species and have contrasting effects on soil microbial respiration.

PubMed

Zwetsloot, Marie J; Kessler, André; Bauerle, Taryn L

2018-04-01

Root-soil interactions fundamentally affect the terrestrial carbon (C) cycle and thereby ecosystem feedbacks to climate change. This study addressed the question of whether the secondary metabolism of different temperate forest tree species can affect soil microbial respiration. We hypothesized that phenolics can both increase and decrease respiration depending on their function as food source, mobilizer of other soil resources, signaling compound, or toxin. We analyzed the phenolic compounds from root exudates and root tissue extracts of six tree species grown in a glasshouse using high-performance liquid chromatography. We then tested the effect of individual phenolic compounds, representing the major identified phenylpropanoid compound classes, on microbial respiration through a 5-d soil incubation. Phenolic root profiles were highly species-specific. Of the eight classes identified, flavonoids were the most abundant, with flavanols being the predominating sub-class. Phenolic effects on microbial respiration ranged from a 26% decrease to a 46% increase, with reduced respiration occurring in the presence of compounds possessing a catechol ring. Tree species variation in root phenolic composition influences the magnitude and direction of root effects on microbial respiration. Our data support the hypothesis that functional group rather than biosynthetic class determines the root phenolic effect on soil C cycling. © 2018 The Authors. New Phytologist © 2018 New Phytologist Trust.

Optimization of pressurized liquid extraction by response surface methodology of Goji berry (Lycium barbarum L.) phenolic bioactive compounds.

PubMed

Tripodo, Giusy; Ibáñez, Elena; Cifuentes, Alejandro; Gilbert-López, Bienvenida; Fanali, Chiara

2018-01-03

Pressurized liquid extraction (PLE) has been used for the first time in this work to extract phenolic compounds from Goji berries according to a multilevel factorial design using response surface methodology. The global yield (% w/dw, weight/dry-weight), total phenolic content (TPC), total flavonoid (TF) and antioxidant activity (determined via ABTS assay, expressed as TEAC value) were used as response variables to study the effects of temperature (50-180°C) and green solvent composition (mixtures of ethanol/water). Phenolic compounds characterization was performed by high performance liquid chromatography-diode array detector-tandem mass spectrometry (HPLC-DAD-MS/MS). The optimum PLE conditions predicted by the model were as follows: 180°C and 86% ethanol in water with a good desirability value of 0.815. The predicted conditions were confirmed experimentally and once the experimental design was validated for commercial fruit samples, the PLE extraction of phenolic compounds from three different varieties of fruit samples (Selvatico mongolo, Bigol, and Polonia) was performed. Nine phenolic compounds were tentatively identified in these extracts, including phenolic acids and their derivatives, and flavonols. The optimized PLE conditions were compared to a conventional solid-liquid extraction, demonstrating that PLE is a useful alternative to extract phenolic compounds from Goji berry. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Phenolic compounds can delay the oxidation of polyunsaturated fatty acids and the growth of Listeria monocytogenes: structure-activity relationships.

PubMed

Pernin, Aurélia; Dubois-Brissonnet, Florence; Roux, Stéphanie; Masson, Marine; Bosc, Véronique; Maillard, Marie-Noëlle

2018-04-20

Phenolic compounds present a potential solution to ensuring food quality and safety. Indeed, they can limit oxidation reactions and bacterial growth in food products. Although their antioxidant mechanisms of action are well known, their antibacterial ones are less well understood, especially in light of their chemical structures. The aim of this study was to first quantify both aspects of a series of natural phenolic compounds and then link these activities to their chemical structure. We evaluated antioxidant activity by measuring the capacity of phenolic compounds to delay free linoleic acid oxidation caused by the action of a hydrophilic azo-radical initiator (AAPH). We evaluated antibacterial activity by measuring the growth inhibition of Listeria monocytogenes and determining the non-inhibitory and minimum inhibitory concentrations for each compound. Compounds with ortho-diphenolic structures were the best antioxidants, whereas those belonging to the simple phenol category were the best antibacterial compounds. The physico-chemical properties of the compounds influenced both activities, but not in the same way. The chemical environment of the phenolic group and the presence of delocalization structures are the most important parameters for antioxidant activity, whereas the partition coefficient logP is one of the most important factors involved in antibacterial activity. This article is protected by copyright. All rights reserved.

Fast pyrolysis of palm kernel shells: influence of operation parameters on the bio-oil yield and the yield of phenol and phenolic compounds.

PubMed

Kim, Seon-Jin; Jung, Su-Hwa; Kim, Joo-Sik

2010-12-01

Palm kernel shells were pyrolyzed in a pyrolysis plant equipped with a fluidized-bed reactor and a char-separation system. The influence of reaction temperature, feed size and feed rate on the product spectrum was also investigated. In addition, the effect of reaction temperature on the yields of phenol and phenolic compounds in the bio-oil was examined. The maximum bio-oil yield was 48.7 wt.% of the product at 490 degrees C. The maximum yield of phenol plus phenolic compounds amounted to about 70 area percentage at 475 degrees C. The yield of pyrolytic lignin after its isolation from the bio-oil was approximately 46 wt.% based on the water and ash free oil. The pyrolytic lignin was mainly composed of phenol, phenolic compounds and oligomers of coniferyl, sinapyl and p-coumaryl alcohols. From the result of a GPC analysis, the number average molecular weight and the weight average molecular weight were 325 and 463 g/mol, respectively. 2010 Elsevier Ltd. All rights reserved.

Analysis of Protein-Phenolic Compound Modifications Using Electrochemistry Coupled to Mass Spectrometry.

PubMed

Kallinich, Constanze; Schefer, Simone; Rohn, Sascha

2018-01-29

In the last decade, electrochemical oxidation coupled with mass spectrometry has been successfully used for the analysis of metabolic studies. The application focused in this study was to investigate the redox potential of different phenolic compounds such as the very prominent chlorogenic acid. Further, EC/ESI-MS was used as preparation technique for analyzing adduct formation between electrochemically oxidized phenolic compounds and food proteins, e.g., alpha-lactalbumin or peptides derived from a tryptic digestion. In the first step of this approach, two reactant solutions are combined and mixed: one contains the solution of the digested protein, and the other contains the phenolic compound of interest, which was, prior to the mixing process, electrochemically transformed to several oxidation products using a boron-doped diamond working electrode. As a result, a Michael-type addition led to covalent binding of the activated phenolic compounds to reactive protein/peptide side chains. In a follow-up approach, the reaction mix was further separated chromatographically and finally detected using ESI-HRMS. Compound-specific, electrochemical oxidation of phenolic acids was performed successfully, and various oxidation and reaction products with proteins/peptides were observed. Further optimization of the reaction (conditions) is required, as well as structural elucidation concerning the final adducts, which can be phenolic compound oligomers, but even more interestingly, quite complex mixtures of proteins and oxidation products.

Effect of drying of figs (Ficus carica L.) on the contents of sugars, organic acids, and phenolic compounds.

PubMed

Slatnar, Ana; Klancar, Urska; Stampar, Franci; Veberic, Robert

2011-11-09

Fresh figs were subjected to two different drying processes: sun-drying and oven-drying. To assess their effect on the nutritional and health-related properties of figs, sugars, organic acids, single phenolics, total phenolics, and antioxidant activity were determined before and after processing. Samples were analyzed three times in a year, and phenolic compounds were determined using high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS). In figs, monomer sugars predominate, which is important nutritional information, and the content of sugars as well as organic acids in fresh figs was lower than in dried fruits. However, the best sugar/organic acid ratio was measured after the sun-drying process. Analysis of individual phenolic compounds revealed a higher content of all phenolic groups determined after the oven-drying process, with the exception of cyanidin-3-O-rutinoside. Similarly, higher total phenolic content and antioxidant activity were detected after the drying process. With these results it can be concluded that the differences in analyzed compounds in fresh and dried figs are significant. The differences between the sun-dried and oven-dried fruits were determined in organic acids, sugars, chlorogenic acid, catechin, epicatechin, kaempferol-3-O-glucoside, luteolin-8-C-glucoside, and total phenolic contents. The results indicate that properly dried figs can be used as a good source of phenolic compounds.

Phenolic compounds participating in mulberry juice sediment formation during storage.

PubMed

Zou, Bo; Xu, Yu-Juan; Wu, Ji-Jun; Yu, Yuan-Shan; Xiao, Geng-Sheng

The stability of clarified juice is of great importance in the beverage industry and to consumers. Phenolic compounds are considered to be one of the main factors responsible for sediment formation. The aim of this study is to investigate the changes in the phenolic content in clarified mulberry juice during storage. Hence, separation, identification, quantification, and analysis of the changes in the contents of phenolic compounds, both free and bound forms, in the supernatant and sediments of mulberry juice, were carried out using high performance liquid chromatographic system, equipped with a photo-diode array detector (HPLC-PDA) and HPLC coupled with quadrupole-time of flight mass spectrometric (HPLC-QTOF-MS/MS) techniques. There was an increase in the amount of sediment formed over the period of study. Total phenolic content of supernatant, as well as free phenolic content in the extracts of the precipitate decreased, whereas the bound phenolic content in the sediment increased. Quantitative estimation of individual phenolic compounds indicated high degradation of free anthocyanins in the supernatant and sediment from 938.60 to 2.30 mg/L and 235.60 to 1.74 mg/g, respectively. A decrease in flavonoids in the supernatant was also observed, whereas the contents of bound forms of gallic acid, protocatechuic acid, caffeic acid, and rutin in the sediment increased. Anthocyanins were the most abundant form of phenolics in the sediment, and accounted for 67.2% of total phenolics after 8 weeks of storage. These results revealed that phenolic compounds, particularly anthocyanins, were involved in the formation of sediments in mulberry juice during storage.

Optimization of drying process and pressurized liquid extraction for recovery of bioactive compounds from avocado peel by-product.

PubMed

Figueroa, Jorge G; Borrás-Linares, Isabel; Lozano-Sánchez, Jesús; Quirantes-Piné, Rosa; Segura-Carretero, Antonio

2018-04-16

The aim of the present study was to optimize the extraction of phenolic compounds in avocado peel using pressurized liquid extraction (PLE) with GRAS solvents. Response surface methodology (RSM) based on Central Composite Design 2 2 model was used in order to optimize PLE conditions. Moreover, the effect of air drying temperature on the total polyphenol content (TPC) and individual phenolic compounds concentration were evaluated. The quantification of individual compounds was performed by HPLC-DAD-ESI-TOF-MS. The optimized extraction conditions were 200°C as extraction temperature and 1:1 v/v as ethanol/water ratio. Regarding to the effect of drying, the highest TPC was obtained with a drying temperature of 85°C. Forty seven phenolic compounds were quantified in the obtained extracts, showing that phenolic acids found to be the more stables compounds to drying process, while procyanidins were the more thermolabiles analytes. To our knowledge, this is the first available study in which phenolic compounds extraction was optimized using PLE and such amount of phenolic compounds was quantified in avocado peel. These results confirm that PLE represents a powerful tool to obtain avocado peel extracts with high concentration in bioactive compounds suitable for its use in the food, cosmetic or pharmaceutical sector. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Altered Transport and Metabolism of Phenolic Compounds in Obesity and Diabetes: Implications for Functional Food Development and Assessment.

PubMed

Redan, Benjamin W; Buhman, Kimberly K; Novotny, Janet A; Ferruzzi, Mario G

2016-11-01

Interest in the application of phenolic compounds from the diet or supplements for the prevention of chronic diseases has grown substantially, but the efficacy of such approaches in humans is largely dependent on the bioavailability and metabolism of these compounds. Although food and dietary factors have been the focus of intense investigation, the impact of disease states such as obesity or diabetes on their absorption, metabolism, and eventual efficacy is important to consider. These factors must be understood in order to develop effective strategies that leverage bioactive phenolic compounds for the prevention of chronic disease. The goal of this review is to discuss the inducible metabolic systems that may be influenced by disease states and how these effects impact the bioavailability and metabolism of dietary phenolic compounds. Because current studies generally report that obesity and/or diabetes alter the absorption and excretion of these compounds, this review includes a description of the absorption, conjugation, and excretion pathways for phenolic compounds and how they are potentially altered in disease states. A possible mechanism that will be discussed related to the modulation of phenolic bioavailability and metabolism may be linked to increased inflammatory status from increased amounts of adipose tissue or elevated plasma glucose concentrations. Although more studies are needed, the translation of benefits derived from dietary phenolic compounds to individuals with obesity or diabetes may require the consideration of dosing strategies or be accompanied by adjunct therapies to improve the bioavailability of these compounds. © 2016 American Society for Nutrition.

Altered Transport and Metabolism of Phenolic Compounds in Obesity and Diabetes: Implications for Functional Food Development and Assessment12

PubMed Central

Redan, Benjamin W; Buhman, Kimberly K; Novotny, Janet A; Ferruzzi, Mario G

2016-01-01

Interest in the application of phenolic compounds from the diet or supplements for the prevention of chronic diseases has grown substantially, but the efficacy of such approaches in humans is largely dependent on the bioavailability and metabolism of these compounds. Although food and dietary factors have been the focus of intense investigation, the impact of disease states such as obesity or diabetes on their absorption, metabolism, and eventual efficacy is important to consider. These factors must be understood in order to develop effective strategies that leverage bioactive phenolic compounds for the prevention of chronic disease. The goal of this review is to discuss the inducible metabolic systems that may be influenced by disease states and how these effects impact the bioavailability and metabolism of dietary phenolic compounds. Because current studies generally report that obesity and/or diabetes alter the absorption and excretion of these compounds, this review includes a description of the absorption, conjugation, and excretion pathways for phenolic compounds and how they are potentially altered in disease states. A possible mechanism that will be discussed related to the modulation of phenolic bioavailability and metabolism may be linked to increased inflammatory status from increased amounts of adipose tissue or elevated plasma glucose concentrations. Although more studies are needed, the translation of benefits derived from dietary phenolic compounds to individuals with obesity or diabetes may require the consideration of dosing strategies or be accompanied by adjunct therapies to improve the bioavailability of these compounds. PMID:28140326

Chemical composition and antibacterial activities of lupin seeds extracts.

PubMed

Lampart-Szczapa, Eleonora; Siger, Aleksander; Trojanowska, Krystyna; Nogala-Kalucka, Małgorzata; Malecka, Maria; Pacholek, Bogdan

2003-10-01

Determination of influence of lupin natural phenolic compounds on antibacterial properties of its seeds was carried out. Raw material were seeds of Lupinus albus, L. luteus, and L. angustifolius. The methods included the determination of the content of proteins, total phenolic compounds, free phenolic acids, and tannins as well as antibacterial properties with ethanol extracts. The content of total phenolic compounds was smaller in testas than in cotyledons and the highest levels are observed in bitter cultivars of Lupinus albus cv. Bac and L. angustifolius cv. Mirela. Lupin tannins mainly occurred in cotyledons of the white lupin, predominantly in the bitter cultivar Bac. Free phenolic acids were mainly found in testas. Only extracts from the testas displayed antibacterial properties, which excludes the possibility of alkaloid influence on the results. The results suggest that inhibition of test bacteria growth depended mainly upon the content of the total phenolic compounds.

Phenol-selective mass spectrometric analysis of jet fuel.

PubMed

Zhu, Haoxuan; Janusson, Eric; Luo, Jingwei; Piers, James; Islam, Farhana; McGarvey, G Bryce; Oliver, Allen G; Granot, Ori; McIndoe, J Scott

2017-08-21

Bromobenzyl compounds react selectively with phenols via the Williamson ether synthesis. An imidazolium charge-tagged bromobenzyl compound can be used to reveal phenol impurities in jet fuel by analysis via electrospray ionization mass spectrometry. The complex matrix as revealed by Cold EI GC/MS analysis is reduced to a few simple sets of compounds in the charge-tagged ESI mass spectrum, primarily substituted phenols and thiols. Examination of jet fuels treated by different refinery methods reveals the efficacy of these approaches in removing these contaminants.

Development of Phenol-Enriched Olive Oil with Phenolic Compounds Extracted from Wastewater Produced by Physical Refining.

PubMed

Venturi, Francesca; Sanmartin, Chiara; Taglieri, Isabella; Nari, Anita; Andrich, Gianpaolo; Terzuoli, Erika; Donnini, Sandra; Nicolella, Cristiano; Zinnai, Angela

2017-08-22

While in the last few years the use of olive cake and mill wastewater as natural sources of phenolic compounds has been widely considered and several studies have focused on the development of new extraction methods and on the production of functional foods enriched with natural antioxidants, no data has been available on the production of a phenol-enriched refined olive oil with its own phenolic compounds extracted from wastewater produced during physical refining. In this study; we aimed to: (i) verify the effectiveness of a multi-step extraction process to recover the high-added-value phenolic compounds contained in wastewater derived from the preliminary washing degumming step of the physical refining of vegetal oils; (ii) evaluate their potential application for the stabilization of olive oil obtained with refined olive oils; and (iii) evaluate their antioxidant activity in an in vitro model of endothelial cells. The results obtained demonstrate the potential of using the refining wastewater as a source of bioactive compounds to improve the nutraceutical value as well as the antioxidant capacity of commercial olive oils. In the conditions adopted, the phenolic content significantly increased in the prototypes of phenol-enriched olive oils when compared with the control oil.

Extraction, Separation, and Identification of Phenolic Compounds in Virgin Olive Oil by HPLC-DAD and HPLC-MS

PubMed Central

Tasioula-Margari, Maria; Tsabolatidou, Eleftheria

2015-01-01

The aim of this study was to evaluate the recovery of individual phenolic compounds extracted from virgin olive oil (VOO), from different Greek olive varieties. Sufficient recoveries (90%) of all individual phenolic compounds were obtained using methanol as an extraction solvent, acetonitrile for residue solubilization, and two washing steps with hexane. Moreover, in order to elucidate structural characteristics of phenolic compounds in VOO, high performance liquid chromatography with a diode array detector (HPLC-DAD) at 280 and 340 nm and HPLC coupled to electrospray ionization mass spectrometry (HPLC-ESI-MS) in the negative-ion mode were performed. The most abundant phenolic compounds were oleuropein derivatives with m/z 319 and 377 and ligstroside derivatives with m/z 303, 361. Lignans, such as 1-acetoxypinoresinol and pinoresinol were also present in substantial quantities in the phenolic fraction. However, pinoresinol was co-eluted with dialdehydic form of ligstroside aglycone (DAFLA) and it was not possible to be quantified separately. The phenolic extracts, obtained from different VOO samples, yielded similar HPLC profiles. Differences, however, were observed in the last part of the chromatogram, corresponding to isomers of the aldehydic form of ligstroside aglycone. Oxidized phenolic products, originating from secoiridoids, were also detected. PMID:26783843

Occurrence, Ecological and Human Health Risks, and Seasonal Variations of Phenolic Compounds in Surface Water and Sediment of a Potential Polluted River Basin in China.

PubMed

Zhou, Mo; Zhang, Jiquan; Sun, Caiyun

2017-09-27

Five phenolic compounds in water and sediment of Yinma River Basin were investigated. The average concentration of phenol was the highest in water samples as well as in sediment samples during the wet season, 101.68 ng/L and 127.76 ng/g, respectively. 2,4,6-Trichlorophenol (2,4,6-TCP) and pentachlorophenol (PCP) was not detected in some sampling sites. Shitou Koumen Reservoir and the neighboring area were the severest areas of phenolic pollution. The lower reach was more polluted in three water seasons than the middle reach and upper reach. Phenol had ecological risks in sediment during three water seasons. 2-Nitrophenol (2-NP) and 2,4-dichlorophenol (2,4-DCP) had ecological risks in sediment in both the normal and wet season. The concentrations of five phenolic compounds from high to low were in the wet season, normal season, and dry season in water and sediment, respectively. There were middle risks in water of total concentrations for five phenolic compounds in several sampling sites. Total concentrations for five phenolic compounds in sediment had high ecological risks in all sampling sites. However, there was no human health risk in the Yinma River Basin.

Development of Phenol-Enriched Olive Oil with Phenolic Compounds Extracted from Wastewater Produced by Physical Refining

PubMed Central

Taglieri, Isabella; Nari, Anita; Andrich, Gianpaolo; Terzuoli, Erika; Donnini, Sandra; Nicolella, Cristiano; Zinnai, Angela

2017-01-01

While in the last few years the use of olive cake and mill wastewater as natural sources of phenolic compounds has been widely considered and several studies have focused on the development of new extraction methods and on the production of functional foods enriched with natural antioxidants, no data has been available on the production of a phenol-enriched refined olive oil with its own phenolic compounds extracted from wastewater produced during physical refining. In this study; we aimed to: (i) verify the effectiveness of a multi-step extraction process to recover the high-added-value phenolic compounds contained in wastewater derived from the preliminary washing degumming step of the physical refining of vegetal oils; (ii) evaluate their potential application for the stabilization of olive oil obtained with refined olive oils; and (iii) evaluate their antioxidant activity in an in vitro model of endothelial cells. The results obtained demonstrate the potential of using the refining wastewater as a source of bioactive compounds to improve the nutraceutical value as well as the antioxidant capacity of commercial olive oils. In the conditions adopted, the phenolic content significantly increased in the prototypes of phenol-enriched olive oils when compared with the control oil. PMID:28829365

Occurrence, Ecological and Human Health Risks, and Seasonal Variations of Phenolic Compounds in Surface Water and Sediment of a Potential Polluted River Basin in China

PubMed Central

Zhou, Mo; Sun, Caiyun

2017-01-01

Five phenolic compounds in water and sediment of Yinma River Basin were investigated. The average concentration of phenol was the highest in water samples as well as in sediment samples during the wet season, 101.68 ng/L and 127.76 ng/g, respectively. 2,4,6-Trichlorophenol (2,4,6-TCP) and pentachlorophenol (PCP) was not detected in some sampling sites. Shitou Koumen Reservoir and the neighboring area were the severest areas of phenolic pollution. The lower reach was more polluted in three water seasons than the middle reach and upper reach. Phenol had ecological risks in sediment during three water seasons. 2-Nitrophenol (2-NP) and 2,4-dichlorophenol (2,4-DCP) had ecological risks in sediment in both the normal and wet season. The concentrations of five phenolic compounds from high to low were in the wet season, normal season, and dry season in water and sediment, respectively. There were middle risks in water of total concentrations for five phenolic compounds in several sampling sites. Total concentrations for five phenolic compounds in sediment had high ecological risks in all sampling sites. However, there was no human health risk in the Yinma River Basin. PMID:28953252

Metabolic and Microbial Modulation of the Large Intestine Ecosystem by Non-Absorbed Diet Phenolic Compounds: A Review.

PubMed

Mosele, Juana I; Macià, Alba; Motilva, Maria-José

2015-09-18

Phenolic compounds represent a diverse group of phytochemicals whose intake is associated with a wide spectrum of health benefits. As consequence of their low bioavailability, most of them reach the large intestine where, mediated by the action of local microbiota, a series of related microbial metabolites are accumulated. In the present review, gut microbial transformations of non-absorbed phenolic compounds are summarized. Several studies have reached a general consensus that unbalanced diets are associated with undesirable changes in gut metabolism that could be detrimental to intestinal health. In terms of explaining the possible effects of non-absorbed phenolic compounds, we have also gathered information regarded their influence on the local metabolism. For this purpose, a number of issues are discussed. Firstly, we consider the possible implications of phenolic compounds in the metabolism of colonic products, such as short chain fatty acids (SCFA), sterols (cholesterol and bile acids), and microbial products of non-absorbed proteins. Due to their being recognized as affective antioxidant and anti-inflammatory agents, the ability of phenolic compounds to counteract or suppress pro-oxidant and/or pro-inflammatory responses, triggered by bowel diseases, is also presented. The modulation of gut microbiota through dietetic maneuvers including phenolic compounds is also commented on. Although the available data seems to assume positive effects in terms of gut health protection, it is still insufficient for solid conclusions to be extracted, basically due to the lack of human trials to confirm the results obtained by the in vitro and animal studies. We consider that more emphasis should be focused on the study of phenolic compounds, particularly in their microbial metabolites, and their power to influence different aspects of gut health.

Phenolic Compounds in Apple (Malus x domestica Borkh.): Compounds Characterization and Stability during Postharvest and after Processing

PubMed Central

Francini, Alessandra; Sebastiani, Luca

2013-01-01

This paper summarizes the information on the occurrence of phenolic compounds in apple (Malus x domestica Borkh.) fruit and juice, with special reference to their health related properties. As phytochemical molecules belonging to polyphenols are numerous, we will focus on the main apples phenolic compounds with special reference to changes induced by apple cultivar, breeding approaches, fruit postharvest and transformation into juice. PMID:26784345

Antibacterial Potential of Northeastern Portugal Wild Plant Extracts and Respective Phenolic Compounds

PubMed Central

Ferreira, Isabel C. F. R.; Barros, Lillian; Carvalho, Ana Maria; Soares, Graça; Henriques, Mariana

2014-01-01

The present work aims to assess the antibacterial potential of phenolic extracts, recovered from plants obtained on the North East of Portugal, and of their phenolic compounds (ellagic, caffeic, and gallic acids, quercetin, kaempferol, and rutin), against bacteria commonly found on skin infections. The disk diffusion and the susceptibility assays were used to identify the most active extracts and phenolic compounds. The effect of selected phenolic compounds on animal cells was assessed by determination of cellular metabolic activity. Gallic acid had a higher activity, against gram-positive (S. epidermidis and S. aureus) and gram-negative bacteria (K. pneumoniae) at lower concentrations, than the other compounds. The caffeic acid, also, showed good antibacterial activity against the 3 bacteria used. The gallic acid was effective against the 3 bacteria without causing harm to the animal cells. Gallic and caffeic acid showed a promising applicability as antibacterial agents for the treatment of infected wounds. PMID:24804249

Development and Validation of an Analytical Methodology Based on Liquid Chromatography-Electrospray Tandem Mass Spectrometry for the Simultaneous Determination of Phenolic Compounds in Olive Leaf Extract.

PubMed

Cittan, Mustafa; Çelik, Ali

2018-04-01

A simple method was validated for the analysis of 31 phenolic compounds using liquid chromatography-electrospray tandem mass spectrometry. Proposed method was successfully applied to the determination of phenolic compounds in an olive leaf extract and 24 compounds were analyzed quantitatively. Olive biophenols were extracted from olive leaves by using microwave-assisted extraction with acceptable recovery values between 78.1 and 108.7%. Good linearities were obtained with correlation coefficients over 0.9916 from calibration curves of the phenolic compounds. The limits of quantifications were from 0.14 to 3.2 μg g-1. Intra-day and inter-day precision studies indicated that the proposed method was repeatable. As a result, it was confirmed that the proposed method was highly reliable for determination of the phenolic species in olive leaf extracts.

The content of phenolic compounds in leaf tissues of white (Aesculus hippocastanum L.) and red horse chestnut (Aesculus carea H.) colonized by the horse chestnut leaf miner (Cameraria ohridella Deschka & Dimić).

PubMed

Oszmiański, Jan; Kalisz, Stanisław; Aneta, Wojdyło

2014-09-15

Normally, plant phenolics are secondary metabolites involved in the defense mechanisms of plants against fungal pathogens. Therefore, in this study we attempted to quantify and characterize phenolic compounds in leaves of white and red horse chestnut with leaf miner larvae before and after Cameraria ohridella attack. A total of 17 phenolic compounds belonging to the hydroxycinnamic acid, flavan-3-ols and flavonol groups were identified and quantified in white and red horse chestnut leaf extracts. Significantly decreased concentrations of some phenolic compounds, especially of flavan-3-ols, were observed in infected leaves compared to the non-infected ones. Additionally, a higher content of polyphenolic compounds especially (-)-epicatechin and procyanidins in leaves of red-flowering than in white-flowering horse chestnut may explain their greater resistance to C. ohridella insects.

Rapid estimation of the oxidative activities of individual phenolics in crude plant extracts.

PubMed

Vihakas, Matti; Pälijärvi, Maija; Karonen, Maarit; Roininen, Heikki; Salminen, Juha-Pekka

2014-07-01

Previous studies of purified phenolic compounds have revealed that some phenolics, especially ellagitannins, can autoxidise under alkaline conditions, which predominate in the midgut of lepidopteran larvae. To facilitate screening for the pro-oxidant activities of all types of phenolic compounds from crude plant extracts, we developed a method that combined our recent spectrophotometric bioactivity method with an additional chromatographic step via UPLC-DAD-MS. This method allowed us to estimate the total pro-oxidant capacities of crude extracts from 12 plant species and to identify the individual phenolic compounds that were responsible for the detected activities. It was found that the pro-oxidant capacities of the plant species (i.e., the concentrations of the easily-oxidised phenolics) varied from 0 to 57 mg/g dry wt, representing from 0% to 46% of the total phenolics from different species. UPLC-DAD-MS analysis revealed that most flavonol and flavone glycosides were only slightly affected by alkaline conditions, thus indicating their low pro-oxidant activity. Interestingly, myricetin-type compounds differed from the other flavonoids, as their concentrations decreased strongly due to alkaline incubation. The same effect was detected for hydrolysable tannins and prodelphinidins, suggesting that a pyrogallol sub-structure could be a key structural component that partially explains their easy oxidation at high pH. Other types of phenolic compounds, such as hydroxycinnamic acids, were relatively active, as well. These findings demonstrate that this method displays the potential to identify most of the active and inactive pro-oxidant phenolic compounds in various plant species. Copyright © 2014 Elsevier Ltd. All rights reserved.

Determination of phenolic compounds using spectral and color transitions of rhodium nanoparticles.

PubMed

Gatselou, Vasiliki; Christodouleas, Dionysios C; Kouloumpis, Antonios; Gournis, Dimitrios; Giokas, Dimosthenis L

2016-08-17

This work reports a new approach for the determination of phenolic compounds based on their interaction with citrate-capped rhodium nanoparticles. Phenolic compounds (i.e., catechins, gallates, cinnamates, and dihydroxybenzoic acids) were found to cause changes in the size and localized surface plasmon resonance of rhodium nanoparticles, and therefore, give rise to analyte-specific spectral and color transitions in the rhodium nanoparticle suspensions. Upon reaction with phenolic compounds (mainly dithydroxybenzoate derivatives, and trihydroxybenzoate derivatives), new absorbance peaks at 350 nm and 450 nm were observed. Upon reaction with trihydroxybenzoate derivatives, however, an additional absorbance peak at 580 nm was observed facilitating the speciation of phenolic compounds in the sample. Both absorbance peaks at 450 nm and 580 nm increased with increasing concentration of phenolic compounds over a linear range of 0-500 μM. Detection limits at the mid-micromolar levels were achieved, depending on the phenolic compound involved, and with satisfactory reproducibility (<7.3%). On the basis of these findings, two rhodium nanoparticles-based assays for the determination of the total phenolic content and total catechin content were developed and applied in tea samples. The obtained results correlated favorably with commonly used methods (i.e., Folin-Ciocalteu and aluminum complexation assay). Not the least, the finding that rhodium nanoparticles can react with analytes and exhibit unique localized surface plasmon resonance bands in the visible region, can open new opportunities for developing new optical and sensing analytical applications. Copyright © 2016 Elsevier B.V. All rights reserved.

Continuous extraction of phenolic compounds from pomegranate peel using high voltage electrical discharge.

PubMed

Xi, Jun; He, Lang; Yan, Liang-Gong

2017-09-01

Pomegranate peel, a waste generated from fruit processing industry, is a potential source of phenolic compounds that are known for their anti-oxidative properties. In this study, a continuous high voltage electrical discharge (HVED) extraction system was for the first time designed and optimized for phenolic compounds from pomegranate peel. The optimal conditions for HVED were: flow rate of materials 12mL/min, electrodes gap distance 3.1mm (corresponding to 29kV/cm of electric field intensity) and liquid to solid ratio 35mL/g. Under these conditions, the experimental yield of phenolic compounds was 196.7±6.4mg/g, which closely agreed with the predicted value (199.83mg/g). Compared with the warm water maceration, HVED method possessed higher efficiency for the extraction of phenolic compounds. The results demonstrated that HVED technique could be a very effective method for continuous extraction of natural compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

The Performance of Four Different Mineral Liners on the Transportation of Chlorinated Phenolic Compounds to Groundwater in Landfills

PubMed Central

Adar, Elanur; Bilgili, Mehmet Sinan

2015-01-01

The aim of this study was to investigate the efficiency of four different mineral liners (clay, bentonite, kaoline, and zeolite) which could be utilized to prevent the transport of phenolic compounds to groundwater through alternative liner systems. Four laboratory-scale HDPE reactors with 80 cm height and 40 cm inner diameter were operated for a period of 180 days. Results indicated that the transport of mono- or dichlorophenols is significantly prevented by the liner systems used, while the transport of highly chlorinated phenolic compounds cannot be prevented by the landfill liner system effectively. Highly chlorinated phenolic compounds in groundwater can be found in higher concentrations than the leachate, as a result of the degradation and transformation of these compounds. Thus, the analysis of highly chlorinated phenolic compounds such as 2,4,6-TCP, 2,3,6-TCP, 3,4,5-TCP, and PCP is of great significance for the studies to be conducted on the contamination of groundwater around landfills. PMID:26759828

Application of Fungicides and Microalgal Phenolic Extracts for the Direct Control of Fumonisin Contamination in Maize.

PubMed

Scaglioni, Priscila Tessmer; Blandino, Massimo; Scarpino, Valentina; Giordano, Debora; Testa, Giulio; Badiale-Furlong, Eliana

2018-05-16

Fungicides and, for the first time, microalgal phenolic extracts (MPE) from Spirulina sp. and Nannochloropsis sp. were applied on maize culture media under field conditions to evaluate their ability to minimize Fusarium species development and fumonisin production. An in vitro assay against F. verticillioides was carried out using maize grains as the culture medium. An open-field experiment was carried out in Northwest Italy under natural infection conditions. The compared treatments were factorial combinations of two insecticide treatments (an untreated control and pyrethroid, used against European Corn Borer), four antifungal treatments (an untreated control, MPE from Spirulina sp., MPE from Nannochloropsis sp., and a synthetic fungicide), and two timings of the application of the antifungal compounds (at maize flowering and at the milk stage). The MPE compounds were capable of inhibiting fumonisin production in vitro more efficiently than tebuconazole. Insecticide application reduced the infection by Fusarium species and subsequent fumonisin contamination. However, fumonisins in maize fields were not significantly controlled by either fungicide or MPE application.

Extraction of phenolic compounds from extra virgin olive oil by a natural deep eutectic solvent: Data on UV absorption of the extracts.

PubMed

Paradiso, Vito Michele; Clemente, Antonia; Summo, Carmine; Pasqualone, Antonella; Caponio, Francesco

2016-09-01

This data article refers to the paper "Towards green analysis of virgin olive oil phenolic compounds: extraction by a natural deep eutectic solvent and direct spectrophotometric detection" [1]. A deep eutectic solvent (DES) based on lactic acid and glucose was used as green solvent for phenolic compounds. Eight standard phenolic compounds were solubilized in the DES. Then, a set of extra virgin olive oil (EVOO) samples (n=65) were submitted to liquid-liquid extraction by the DES. The standard solutions and the extracts were analyzed by UV spectrophotometry. This article reports the spectral data of both the standard solutions and the 65 extracts, as well as the total phenolic content of the corresponding oils, assessed by the Folin-Ciocalteu assay.

Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.

PubMed

Alam, Md Iqbal; Alam, Mohammed A; Alam, Ozair; Nargotra, Amit; Taneja, Subhash Chandra; Koul, Surrinder

2016-05-23

In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Identification and quantification of a major anti-oxidant and anti-inflammatory phenolic compound found in basil, lemon, thyme, mint, oregano, rosemary, sage, and thyme

USDA-ARS?s Scientific Manuscript database

Basil, lemon thyme, mint, oregano, rosemary, sage, and thyme are in the mint family of plants that are used as culinary herbs world-wide. These herbs contain phenolic compounds that are believed to have strong antioxidant and anti-inflammatory activities. Therefore, the major phenolic compounds fr...

Mycorrhizal colonization and plant growth affected by aqueous extract of Artemisia princeps var. orientalis and two phenolic compounds.

PubMed

Yun, K W; Choi, S K

2002-02-01

The effects of an aqueous extract of Artemisia princeps var. orientalis and two phenolic compounds on mycorrhizal colonization and plant growth have been investigated. Greenhouse studies showed that the inhibitory effect of the extract on mycorrhizal colonization and plant growth increased in proportion to the concentration of the extract. When the mycorrhizal test plants were treated with an increasing concentration of phenolic compounds, the mycorrhizal colonization in roots of the test plant and the plant growth were decreased. There were strong indications that mycorrhizal fungi mitigated the inhibitory influence of shoot extract of A. princeps var. orientalis and phenolic compounds.

Importance and Implications of the Production of Phenolic Secondary Metabolites by Endophytic Fungi: A Mini-Review.

PubMed

Negreiros de Carvalho, Patrícia Lunardelli; Silva, Eliane de Oliveira; Chagas-Paula, Daniela Aparecida; Hortolan Luiz, Jaine Honorata; Ikegaki, Masaharu

2016-01-01

In the natural products research, a valuable approach is the prospection of uncommon sources and unexplored habitat. Special attention has been given to endophytic fungi because of their ability to produce new and interesting secondary metabolites, which have several biological applications. The endophytes establish exclusive symbiotic relationships with plants and the metabolic interactions may support the synthesis of some similar valuables compounds. Among secondary metabolites, phenol-derived structures are responsible for several bioactivities such as antioxidant, cytotoxic, antimicrobial, among others. Phenolic compounds might be biosynthesized from the shikimate pathway. Although shikimic acid is a common precursor in plants, it is described as rare in microorganisms. To the best of our knowledge, this is the first review about phenolic compounds produced by endophytic fungi and a comparison has been made with those produced by the plant host. This review covers 124 phenolic secondary metabolites produced by endophytic fungi. Considering the data analyzed by us, only seven of such compounds were isolated from fungi and from their hosts. These observations claim for more attention to phenolic compounds produced by endophytic fungi with a view to understand the real importance of these compounds to endophytes survival.

Nutritional Composition and Antioxidant Capacity in Edible Flowers: Characterisation of Phenolic Compounds by HPLC-DAD-ESI/MSn

PubMed Central

Navarro-González, Inmaculada; González-Barrio, Rocío; García-Valverde, Verónica; Bautista-Ortín, Ana Belén; Periago, María Jesús

2014-01-01

Edible flowers are commonly used in human nutrition and their consumption has increased in recent years. The aim of this study was to ascertain the nutritional composition and the content and profile of phenolic compounds of three edible flowers, monks cress (Tropaeolum majus), marigold (Tagetes erecta) and paracress (Spilanthes oleracea), and to determine the relationship between the presence of phenolic compounds and the antioxidant capacity. Proximate composition, total dietary fibre (TDF) and minerals were analysed according to official methods: total phenolic compounds (TPC) were determined with Folin-Ciocalteu’s reagent, whereas antioxidant capacity was evaluated using Trolox Equivalent Antioxidant Capacity (TEAC) and Oxygen Radical Absorbance Capacity (ORAC) assays. In addition, phenolic compounds were characterised by HPLC-DAD-MSn. In relation to the nutritional value, the edible flowers had a composition similar to that of other plant foods, with a high water and TDF content, low protein content and very low proportion of total fat—showing significant differences among samples. The levels of TPC compounds and the antioxidant capacity were significantly higher in T. erecta, followed by S. oleracea and T. majus. Thirty-nine different phenolic compounds were tentatively identified, with flavonols being the major compounds detected in all samples, followed by anthocyanins and hydroxycynnamic acid derivatives. In T. erecta small proportions of gallotannin and ellagic acid were also identified. PMID:25561232

Processing ‘Ataulfo’ Mango into Juice Preserves the Bioavailability and Antioxidant Capacity of Its Phenolic Compounds

PubMed Central

Quirós-Sauceda, Ana Elena; Chen, C.-Y. Oliver; González-Aguilar, Gustavo A.

2017-01-01

The health-promoting effects of phenolic compounds depend on their bioaccessibility from the food matrix and their consequent bioavailability. We carried out a randomized crossover pilot clinical trial to evaluate the matrix effect (raw flesh and juice) of ‘Ataulfo’ mango on the bioavailability of its phenolic compounds. Twelve healthy male subjects consumed a dose of mango flesh or juice. Blood was collected for six hours after consumption, and urine for 24 h. Plasma and urine phenolics were analyzed by electrochemical detection coupled to high performance liquid chromatography (HPLC-ECD). Five compounds were identified and quantified in plasma. Six phenolic compounds, plus a microbial metabolite (pyrogallol) were quantified in urine, suggesting colonic metabolism. The maximum plasma concentration (Cmax) occurred 2–4 h after consumption; excretion rates were maximum at 8–24 h. Mango flesh contributed to greater protocatechuic acid absorption (49%), mango juice contributed to higher chlorogenic acid absorption (62%). Our data suggests that the bioavailability and antioxidant capacity of mango phenolics is preserved, and may be increased when the flesh is processed into juice. PMID:28961171

Processing 'Ataulfo' Mango into Juice Preserves the Bioavailability and Antioxidant Capacity of Its Phenolic Compounds.

PubMed

Quirós-Sauceda, Ana Elena; Chen, C-Y Oliver; Blumberg, Jeffrey B; Astiazaran-Garcia, Humberto; Wall-Medrano, Abraham; González-Aguilar, Gustavo A

2017-09-29

The health-promoting effects of phenolic compounds depend on their bioaccessibility from the food matrix and their consequent bioavailability. We carried out a randomized crossover pilot clinical trial to evaluate the matrix effect (raw flesh and juice) of 'Ataulfo' mango on the bioavailability of its phenolic compounds. Twelve healthy male subjects consumed a dose of mango flesh or juice. Blood was collected for six hours after consumption, and urine for 24 h. Plasma and urine phenolics were analyzed by electrochemical detection coupled to high performance liquid chromatography (HPLC-ECD). Five compounds were identified and quantified in plasma. Six phenolic compounds, plus a microbial metabolite (pyrogallol) were quantified in urine, suggesting colonic metabolism. The maximum plasma concentration (C max ) occurred 2-4 h after consumption; excretion rates were maximum at 8-24 h. Mango flesh contributed to greater protocatechuic acid absorption (49%), mango juice contributed to higher chlorogenic acid absorption (62%). Our data suggests that the bioavailability and antioxidant capacity of mango phenolics is preserved, and may be increased when the flesh is processed into juice.

Tissue-Specific, Development-Dependent Phenolic Compounds Accumulation Profile and Gene Expression Pattern in Tea Plant [Camellia sinensis

PubMed Central

Li, Weiwei; Zhao, Lei; Meng, Fei; Wang, Yunsheng; Tan, Huarong; Yang, Hua; Wei, Chaoling; Wan, Xiaochun; Gao, Liping; Xia, Tao

2013-01-01

Phenolic compounds in tea plant [Camellia sinensis (L.)] play a crucial role in dominating tea flavor and possess a number of key pharmacological benefits on human health. The present research aimed to study the profile of tissue-specific, development-dependent accumulation pattern of phenolic compounds in tea plant. A total of 50 phenolic compounds were identified qualitatively using liquid chromatography in tandem mass spectrometry technology. Of which 29 phenolic compounds were quantified based on their fragmentation behaviors. Most of the phenolic compounds were higher in the younger leaves than that in the stem and root, whereas the total amount of proanthocyanidins were unexpectedly higher in the root. The expression patterns of 63 structural and regulator genes involved in the shikimic acid, phenylpropanoid, and flavonoid pathways were analyzed by quantitative real-time polymerase chain reaction and cluster analysis. Based on the similarity of their expression patterns, the genes were classified into two main groups: C1 and C2; and the genes in group C1 had high relative expression level in the root or low in the bud and leaves. The expression patterns of genes in C2-2-1 and C2-2-2-1 groups were probably responsible for the development-dependent accumulation of phenolic compounds in the leaves. Enzymatic analysis suggested that the accumulation of catechins was influenced simultaneously by catabolism and anabolism. Further research is recommended to know the expression patterns of various genes and the reason for the variation in contents of different compounds in different growth stages and also in different organs. PMID:23646127

Extraction, identification, fractionation and isolation of phenolic compounds in plants with hepatoprotective effects.

PubMed

Pereira, Carla; Barros, Lillian; Ferreira, Isabel C F R

2016-03-15

The liver is one of the most important organs of human body, being involved in several vital functions and regulation of physiological processes. Given its pivotal role in the excretion of waste metabolites and drugs detoxification, the liver is often subjected to oxidative stress that leads to lipid peroxidation and severe cellular damage. The conventional treatments of liver diseases such as cirrhosis, fatty liver and chronic hepatitis are frequently inadequate due to side effects caused by hepatotoxic chemical drugs. To overcome this problematic paradox, medicinal plants, owing to their natural richness in phenolic compounds, have been intensively exploited concerning their extracts and fraction composition in order to find bioactive compounds that could be isolated and applied in the treatment of liver ailments. The present review aimed to collect the main results of recent studies carried out in this field and systematize the information for a better understanding of the hepatoprotective capacity of medicinal plants in in vitro and in vivo systems. Generally, the assessed plant extracts revealed good hepatoprotective properties, justifying the fractionation and further isolation of phenolic compounds from different parts of the plant. Twenty-five phenolic compounds, including flavonoids, lignan compounds, phenolic acids and other phenolic compounds, have been isolated and identified, and proved to be effective in the prevention and/or treatment of chemically induced liver damage. In this perspective, the use of medicinal plant extracts, fractions and phenolic compounds seems to be a promising strategy to avoid side effects caused by hepatotoxic chemicals. © 2015 Society of Chemical Industry.

Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts--Electrophilic aromatic substitution and oxidation.

PubMed

Criquet, Justine; Rodriguez, Eva M; Allard, Sebastien; Wellauer, Sven; Salhi, Elisabeth; Joll, Cynthia A; von Gunten, Urs

2015-11-15

Phenolic compounds are known structural moieties of natural organic matter (NOM), and their reactivity is a key parameter for understanding the reactivity of NOM and the disinfection by-product formation during oxidative water treatment. In this study, species-specific and/or apparent second order rate constants and mechanisms for the reactions of bromine and chlorine have been determined for various phenolic compounds (phenol, resorcinol, catechol, hydroquinone, phloroglucinol, bisphenol A, p-hydroxybenzoic acid, gallic acid, hesperetin and tannic acid) and flavone. The reactivity of bromine with phenolic compounds is very high, with apparent second order rate constants at pH 7 in the range of 10(4) to 10(7) M(-1) s(-1). The highest value was recorded for the reaction between HOBr and the fully deprotonated resorcinol (k = 2.1 × 10(9) M(-1) s(-1)). The reactivity of phenolic compounds is enhanced by the activating character of the phenolic substituents, e.g. further hydroxyl groups. With the data set from this study, the ratio between the species-specific rate constants for the reactions of chlorine versus bromine with phenolic compounds was confirmed to be about 3000. Phenolic compounds react with bromine or chlorine either by oxidation (electron transfer, ET) or electrophilic aromatic substitution (EAS) processes. The dominant process mainly depends on the relative position of the hydroxyl substituents and the possibility of quinone formation. While phenol, p-hydroxybenzoic acid and bisphenol A undergo EAS, hydroquinone, catechol, gallic acid and tannic acid, with hydroxyl substituents in ortho or para positions, react with bromine by ET leading to quantitative formation of the corresponding quinones. Some compounds (e.g. phloroglucinol) show both partial oxidation and partial electrophilic aromatic substitution and the ratio observed for the pathways depends on the pH. For the reaction of six NOM extracts with bromine, electrophilic aromatic substitution accounted for only 20% of the reaction, and for one NOM extract (Pony Lake fulvic acid) it accounted for <10%. This shows that for natural organic matter samples, oxidation (ET) is far more important than bromine incorporation (EAS). Copyright © 2015 Elsevier Ltd. All rights reserved.

Phenolic compounds in Ross Sea water

NASA Astrophysics Data System (ADS)

Zangrando, Roberta; Barbaro, Elena; Gambaro, Andrea; Barbante, Carlo; Corami, Fabiana; Kehrwald, Natalie; Capodaglio, Gabriele

2016-04-01

Phenolic compounds are semi-volatile organic compounds produced during biomass burning and lignin degradation in water. In atmospheric and paleoclimatic ice cores studies, these compounds are used as biomarkers of wood combustion and supply information on the type of combusted biomass. Phenolic compounds are therefore indicators of paleoclimatic interest. Recent studies of Antarctic aerosols highlighted that phenolic compounds in Antarctica are not exclusively attributable to biomass burning but also derive from marine sources. In order to study the marine contribution to aerosols we developed an analytical method to determine the concentration of vanillic acid, vanillin, p-coumaric acid, syringic acid, isovanillic acid, homovanillic acid, syringaldehyde, acetosyringone and acetovanillone present in dissolved and particle phases in Sea Ross waters using HPLC-MS/MS. The analytical method was validated and used to quantify phenolic compounds in 28 sea water samples collected during a 2012 Ross Sea R/V cruise. The observed compounds were vanillic acid, vanillin, acetovanillone and p-coumaric acid with concentrations in the ng/L range. Higher concentrations of analytes were present in the dissolved phase than in the particle phase. Sample concentrations were greatest in the coastal, surficial and less saline Ross Sea waters near Victoria Land.

Influence of rice straw polyphenols on cellulase production by Trichoderma reesei.

PubMed

Zheng, Wei; Zheng, Qin; Xue, Yiyun; Hu, Jiajun; Gao, Min-Tian

2017-06-01

In this study, we found that during cellulase production by Trichoderma reesei large amounts of polyphenols were released from rice straw when the latter was used as the carbon source. We identified and quantified the phenolic compounds in rice straw and investigated the effects of the phenolic compounds on cellulase production by T. reesei. The phenolic compounds of rice straw mainly consisted of phenolic acids and tannins. Coumaric acid (CA) and ferulic acid (FA) were the predominant phenolic acids, which inhibited cellulase production by T. reesei. When the concentrations of CA and FA in the broth increased to 0.06 g/L, cellulase activity decreased by 23% compared with that in the control culture. Even though the rice straw had a lower tannin than phenolic acid content, the tannins had a greater inhibitory effect than the phenolic acids on cellulase production by T. reesei. Tannin concentrations greater than 0.3 g/L completely inhibited cellulase production. Thus, phenolic compounds, especially tannins are the major inhibitors of cellulase production by T. reesei. Therefore, we studied the effects of pretreatments on the release of phenolic compounds. Ball milling played an important role in the release of FA and CA, and hot water extraction was highly efficient in removing tannins. By combining ball milling with extraction by water, the 2-fold higher cellulase activity than in the control culture was obtained. Copyright © 2017 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Simultaneous optimization of the ultrasound-assisted extraction for phenolic compounds content and antioxidant activity of Lycium ruthenicum Murr. fruit using response surface methodology.

PubMed

Chen, Shasha; Zeng, Zhi; Hu, Na; Bai, Bo; Wang, Honglun; Suo, Yourui

2018-03-01

Lycium ruthenicum Murr. (LR) is a functional food that plays an important role in anti-oxidation due to its high level of phenolic compounds. This study aims to optimize ultrasound-assisted extraction (UAE) of phenolic compounds and antioxidant activities of obtained extracts from LR using response surface methodology (RSM). A four-factor-three-level Box-Behnken design (BBD) was employed to discuss the following extracting parameters: extraction time (X 1 ), ultrasonic power (X 2 ), solvent to sample ratio (X 3 ) and solvent concentration (X 4 ). The analysis of variance (ANOVA) results revealed that the solvent to sample ratio had a significant influence on all responses, while the extraction time had no statistically significant effect on phenolic compounds. The optimum values of the combination of phenolic compounds and antioxidant activities were obtained for X 1 =30min, X 2 =100W, X 3 =40mL/g, and X 4 =33% (v/v). Five phenolic acids, including chlorogenic acid, caffeic acid, syringic acid, p-coumaric acid and ferulic acid, were analyzed by HPLC. Our results indicated that optimization extraction is vital for the quantification of phenolic compounds and antioxidant activity in LR, which may be contributed to large-scale industrial applications and future pharmacological activities research. Copyright © 2017 Elsevier Ltd. All rights reserved.

Process for producing phenolic compounds from lignins

DOEpatents

Agblevor, Foster A.

1998-01-01

A process for the production of low molecular weight phenolic compounds from lignins through the pyrolysis of the lignins in the presence of a strong base. In a preferred embodiment, potassium hydroxide is present in an amount of from about 0.1% to about 5% by weight, the pyrolysis temperature is from about 400.degree. C. to about 600.degree. C. at atmospheric pressure, and the time period for substantial completion of the reaction is from about 1-3 minutes. Examples of low molecular weight phenolic compounds produced include methoxyphenols, non-methoxylated phenols, and mixtures thereof.

Liquid phase in situ hydrodeoxygenation of biomass-derived phenolic compounds to hydrocarbons over bifunctional catalysts

Treesearch

Junfeng Feng; Chung-yun Hse; Zhongzhi Yang; Kui Wang; Jianchun Jiang; Junming Xu

2017-01-01

The objective of this study was to find an effective method for converting renewable biomass-derived phenolic compounds into hydrocarbons bio-fuel via in situ catalytic hydrodeoxygenation. The in situ hydrodeoxygenation of biomass-derived phenolic compounds was carried out in methanol-water solvent over bifunctional catalysts of Raney Ni and HZSM-5 or H-Beta. In the in...

Relationships Between Bioactive Compound Content and
the Antiplatelet and Antioxidant Activities of Six Allium Vegetable Species

PubMed Central

Beretta, Hebe Vanesa; Bannoud, Florencia; Insani, Marina; Berli, Federico; Hirschegger, Pablo; Galmarini, Claudio Rómulo

2017-01-01

Summary Allium sp. vegetables are widely consumed for their characteristic flavour. Additionally, their consumption may provide protection against cardiovascular disease due to their antiplatelet and antioxidant activities. Although antiplatelet and antioxidant activities in Allium sp. are generally recognised, comparative studies of antiplatelet and antioxidant potency among the main Allium vegetable species are lacking. Also, the relationship between organosulfur and phenolic compounds and these biological activities has not been well established. In this study, the in vitro antiplatelet and antioxidant activities of the most widely consumed Allium species are characterised and compared. The species total organosulfur and phenolic content, and the HPLC profiles of 11 phenolic compounds were characterised and used to investigate the relationship between these compounds and antiplatelet and antioxidant activities. Furthermore, antiplatelet activities in chives and shallot have been characterised for the first time. Our results revealed that the strongest antiplatelet agents were garlic and shallot, whereas chives had the highest antioxidant activity. Leek and bunching onion had the weakest both biological activities. Significantly positive correlations were found between the in vitro antiplatelet activity and total organosulfur (R=0.74) and phenolic (TP) content (R=0.73), as well as between the antioxidant activity and TP (R=0.91) and total organosulfur content (R=0.67). Six individual phenolic compounds were associated with the antioxidant activity, with catechin, epigallocatechin and epicatechin gallate having the strongest correlation values (R>0.80). Overall, our results suggest that both organosulfur and phenolic compounds contribute similarly to Allium antiplatelet activity, whereas phenolics, as a whole, are largely responsible for antioxidant activity, with broad variation observed among the contributions of individual phenolic compounds. PMID:28867958

Selection of discrimination marker from various propolis for mapping and identify anti Candida albicans activity

NASA Astrophysics Data System (ADS)

Mahadewi, Alfiani Guntari; Christina, Daisy; Hermansyah, Heri; Wijanarko, Anondho; Farida, Siti; Adawiyah, Robiatul; Rohmatin, Etin; Sahlan, Muhamad

2018-02-01

The increase in fungal resistance against antifungal drugs available in the market will reduce the effectiveness of treatment for Candidiasis. Propolis contains various compounds with antifungal properties Candida albicans, but the content of each type is very diverse. The sample used was Sulawesi propolis type smooth (taken from inside the nest), rough (taken from outside the hive) and mix (a combination of both). Anti-C. albicans molecule marker is a marker compound for selecting propolis with the ability to overcome Candidiasis. The initial step was to test the levels of flavonoids and phenolic by using UV-Vis spectrometry method. It was founded that each sample was not always superior to any substance, so propolis cannot be directly selected. In Phenolic content, mix propolis has the highest value than other 5.109%. In Flavonoid content, propolis smooth has the highest value than other, 16.38%. Furthermore, propolis selected by antifungal activity test with good diffusion method at the concentration propolis 5% either 7%, the inhibitory diameter zone propolis smooth and rough has same value 10 mm. Propolis mix has an advantage while propolis smooth and rough have the same capability range 12 mm and 13 mm. In this study, the phenolic content plays a major role in antifungal cases.

Characterisation and quantification of phenolic compounds of extra-virgin olive oils according to their geographical origin by a rapid and resolutive LC-ESI-TOF MS method.

PubMed

Ouni, Youssef; Taamalli, Ameni; Gómez-Caravaca, Ana Maria; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto; Zarrouk, Mokhtar

2011-08-01

The phenolic compounds present in seven samples of olive fruits were analysed by a rapid and resolutive LC-ESI-TOF MS method. All samples were collected during the normal picking period for olive oil production, in central and south Tunisia, and were obtained from the Oueslati variety cultivated in different olive growing areas. In the Tunisian samples, 22 compounds have been characterised by LC-ESI-TOF MS analysis. Results showed no qualitative differences in the phenolic fractions between virgin olive oils from different geographical region. However, significant quantitative differences were observed in a wide number of phenolic compounds. These results permit to use the phenolic fractions as an indicator of each region. Copyright © 2011 Elsevier Ltd. All rights reserved.

Factors Affecting the Extraction of Intact Ribonucleic Acid from Plant Tissues Containing Interfering Phenolic Compounds

PubMed Central

Newbury, H. John; Possingham, John V.

1977-01-01

Using conventional methods it is impossible to extract RNA as uncomplexed intact molecules from the leaves of grapevines (Vitis vinifera L.) and from a number of woody perennial species that contain high levels of reactive phenolic compounds. A procedure involving the use of high concentrations of the chaotropic agent sodium perchlorate prevents the binding of phenolic compounds to RNA during extraction. Analyses of the phenolics present in plant tissues used in these experiments indicate that there is a poor correlation between the total phenolic content and the complexing of RNA. However, qualitative analyses suggest that proanthocyanidins are involved in the tanning of RNA during conventional extractions. PMID:16660134

Phenolic Composition and Evaluation of the Antimicrobial Activity of Free and Bound Phenolic Fractions from a Peruvian Purple Corn (Zea mays L.) Accession.

PubMed

Gálvez Ranilla, Lena; Christopher, Ashish; Sarkar, Dipayan; Shetty, Kalidas; Chirinos, Rosana; Campos, David

2017-12-01

Beneficial effects on overall gut health by phenolic bioactives-rich foods are potentially due to their modulation of probiotic gut bacteria and antimicrobial activity against pathogenic bacteria. Based on this rationale, the effect of the free and bound phenolic fractions from a Peruvian purple corn accession AREQ-084 on probiotic lactic acid bacteria such as Lactobacillus helveticus and Bifidobacterium longum and the gastric cancer-related pathogen Helicobacter pylori was evaluated. The free and bound phenolic composition was also determined by ultra-performance liquid chromatography. Anthocyanins were the major phenolic compounds (310.04 mg cyanidin-3-glucoside equivalents/100 g dry weight, DW) in the free phenolic fraction along with hydroxycinnamic acids such as p-coumaric acid derivatives, followed by caffeic and ferulic acid derivatives. The bound phenolic form had only hydroxycinnamic acids such as ferulic acid, p-coumaric acid, and a ferulic acid derivative with ferulic acid being the major phenolic compound (156.30 mg/100 g DW). These phenolic compounds were compatible with beneficial probiotic lactic acid bacteria such as L. helveticus and B. longum as these bacteria were not inhibited by the free and bound phenolic fractions at 10 to 50 mg/mL and 10 mg/mL of sample doses, respectively. However, the pathogenic H. pylori was also not inhibited by both purple corn phenolic forms at same above sample doses. This study provides the preliminary base for the characterization of phenolic compounds of Peruvian purple corn biodiversity and its potential health benefits relevant to improving human gut health. This study provides insights that Peruvian purple corn accession AREQ-084 can be targeted as a potential source of health-relevant phenolic compounds such as anthocyanins along with hydroxycinnamic acids linked to its dietary fiber fraction. Additionally, these phenolic fractions did not affect the gut health associated beneficial bacteria nor the pathogenic H. pylori. Purple corn can be targeted for design of probiotic functional foods integrated with their anthocyanin linked-coloring properties. © 2017 Institute of Food Technologists®.

Influence of Fermentation with Different Lactic Acid Bacteria and in Vitro Digestion on the Biotransformation of Phenolic Compounds in Fermented Pomegranate Juices.

PubMed

Valero-Cases, Estefanía; Nuncio-Jáuregui, Nallely; Frutos, María José

2017-08-09

This study describes the effect of fermentation and the impact of simulated gastrointestinal digestion (SGD) of four fermented pomegranate juices with different lactic acid bacteria (LAB) on the biotransformation of phenolic compounds. The changes of the antioxidant capacity (AOC) and of LAB growth and survival in different fermented juices were also studied. Two new phenolic derivatives (catechin and α-punicalagin) were identified only in fermented juices. During SGD, the AOC increased together with the phenolic derivatives concentration mainly in the juices fermented with Lactobacillus. These derivatives were formed due to the LAB metabolism of the ellagitannins, epicatechin, and catechin after fermentation and during SGD. The FRAP assay performance might be associated with the degradation and biotransformation of catechin. The fermented pomegranate juices with these LAB increased the bioaccessibility of phenolic compounds, ensuring the survival of LAB after SGD, suggesting a possible prebiotic effect of phenolic compounds on LAB.

Chemometric analysis for the evaluation of phenolic patterns in olive leaves from six cultivars at different growth stages.

PubMed

Talhaoui, Nassima; Gómez-Caravaca, Ana María; Roldán, Cristina; León, Lorenzo; De la Rosa, Raúl; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2015-02-18

Leaves from six important olive cultivars grown under the same agronomic conditions were collected at four different times from June to December and analyzed by high performance liquid chromatography-diode array detector-time-of-flight-mass spectrometry (HPLC-DAD-TOF-MS). Twenty-eight phenolic compounds were identified and quantified. No qualitative differences were detected among leaves. However, for all cultivars, total concentrations of phenolic compounds decreased from June to August, then increased from October on, and reached higher levels again in December. Principal component analysis provided a clear separation of the phenolic content in leaves for different sampling times and cultivars. Hence, the availability of phenolic compounds depends on both the season and the cultivar. June and December seem to be good times to collect leaves as a source of phenolic compounds. December coincides with the harvest period of olives in the Andalusian region. Thus, in December olive leaves could be valorized efficiently as olive byproducts.

Protective effect of Spirulina platensis enriched in phenolic compounds against hepatotoxicity induced by CCl4.

PubMed

Kepekçi, Remziye Aysun; Polat, Sait; Çelik, Ahmet; Bayat, Nuray; Saygideger, Saadet Demirörs

2013-12-01

Phenolic compounds make up the major secondary metabolites with high pharmaceutical potential. Microalgae were reported to contain low amounts of phenolic compounds. The present study aimed to investigate the hepatoprotective potential of biomass of Spirulina platensis enriched in phenolic compounds. The protective effects of the biomass of S. platensis with low amounts of phenolics (SP1) and with high amounts of phenolics (SP2) against CCl4-induced acute hepatotoxicity were evaluated in rats. The increased levels of ALT, AST and MDA along with decreased activities of SOD and CAT were significantly (p<0.01) ameliorated by SP2. Histological examinations revealed that SP2 was more potent than SP1 in protecting the liver from toxic injury of CCl4 and preserving the hepatocyte ultrastructure. The lesions including necrosis, lymphocyte infiltration, ballooning degeneration and hepatocyte injury as irregular lamellar organisation, dilations in endoplasmic reticulums and the presence of great number of cytoplasmic vacuolization were healed by SP2. Copyright © 2013 Elsevier Ltd. All rights reserved.

Phenolic compounds and antioxidant activity of kernels and shells of Mexican pecan (Carya illinoinensis).

PubMed

de la Rosa, Laura A; Alvarez-Parrilla, Emilio; Shahidi, Fereidoon

2011-01-12

The phenolic composition and antioxidant activity of pecan kernels and shells cultivated in three regions of the state of Chihuahua, Mexico, were analyzed. High concentrations of total extractable phenolics, flavonoids, and proanthocyanidins were found in kernels, and 5-20-fold higher concentrations were found in shells. Their concentrations were significantly affected by the growing region. Antioxidant activity was evaluated by ORAC, DPPH•, HO•, and ABTS•-- scavenging (TAC) methods. Antioxidant activity was strongly correlated with the concentrations of phenolic compounds. A strong correlation existed among the results obtained using these four methods. Five individual phenolic compounds were positively identified and quantified in kernels: ellagic, gallic, protocatechuic, and p-hydroxybenzoic acids and catechin. Only ellagic and gallic acids could be identified in shells. Seven phenolic compounds were tentatively identified in kernels by means of MS and UV spectral comparison, namely, protocatechuic aldehyde, (epi)gallocatechin, one gallic acid-glucose conjugate, three ellagic acid derivatives, and valoneic acid dilactone.

Characterization of total antioxidant capacity and (poly)phenolic compounds of differently pigmented rice varieties and their changes during domestic cooking.

PubMed

Zaupa, Maria; Calani, Luca; Del Rio, Daniele; Brighenti, Furio; Pellegrini, Nicoletta

2015-11-15

In the recent years, the pigmented rice varieties are becoming more popular due to their antioxidant properties and phenolic content. In this study, we characterized the antioxidant capacity (TAC) and the phenolic profile in white, red and black rice varieties, and evaluated the effect of two cooking methods (i.e. "risotto" and boiling) on these compounds. Before the cooking, all the varieties contained several phenolic acids, whereas anthocyanins and flavonols were peculiar of black rice and flavan-3-ols of red rice. Among the rice varieties, the black had the highest TAC value. The content of (poly)phenolic compounds and TAC decreased after cooking in all three varieties, but to a lesser extent after the risotto method. As a consequence, the risotto cooking, which allows a complete absorption of water, would be a good cooking method to retain (poly)phenolic compounds and TAC in pigmented and non-pigmented whole-meal rice. Copyright © 2015 Elsevier Ltd. All rights reserved.

Effect of cultivar and variety on phenolic compounds and antioxidant activity of cherry wine.

PubMed

Xiao, Zuobing; Fang, Lingling; Niu, Yunwei; Yu, Haiyan

2015-11-01

To compare the influence of cultivar and variety on the phenolic compounds and antioxidant activity (AA) of cherry wines, total phenolic (TP), total flavonoid (TF), total anthocyanin (TA), total tannin (TT), five individual phenolic acids, and AA were determined. An ultra-performance liquid chromatography tandem mass spectrometry (HPLC-DAD/ESI-MS) method was developed for the determination of gallic acid (GAE), p-hydroxybenzoic acid (PHB), chlorogenic acid (CHL), vanillic acid (VAN), and caffeic acid (CAF). A principal component analysis (PCA) and a cluster analysis (CA) were used to analyze differences related to cultivar and variety. The TP, TF, TA, TT, and AA of samples sourced from the Shandong province of China were higher than those from the Jiangsu province. The PCA and CA results showed that phenolic compounds in cherry wines were closely related to cultivar and variety and that cultivar had more influence on the phenolic compounds of cherry wines than variety. Copyright © 2015 Elsevier Ltd. All rights reserved.

Characterization and quantitation of low and high molecular weight phenolic compounds in apple seeds.

PubMed

Fromm, Matthias; Bayha, Sandra; Carle, Reinhold; Kammerer, Dietmar R

2012-02-08

The phenolic constituents of seeds of 12 different apple cultivars were fractionated by sequential extraction with aqueous acetone (30:70, v/v) and ethyl acetate after hexane extraction of the lipids. Low molecular weight phenolic compounds were individually quantitated by RP-HPLC-DAD. The contents of extractable and nonextractable procyanidins were determined by applying RP-HPLC following thiolysis and n-butanol/HCl hydrolysis, respectively. As expected, the results revealed marked differences of the ethyl acetate extracts, aqueous acetone extracts, and insoluble residues with regard to contents and mean degrees of polymerization of procyanidins. Total phenolic contents in the defatted apple seed residues ranged between 18.4 and 99.8 mg/g. Phloridzin was the most abundant phenolic compound, representing 79-92% of monomeric polyphenols. Yields of phenolic compounds significantly differed among the cultivars under study, with seeds of cider apples generally being richer in phloridzin and catechins than seeds of dessert apple cultivars. This is the first study presenting comprehensive data on the contents of phenolic compounds in apple seeds comprising extractable and nonextractable procyanidins. Furthermore, the present work points out a strategy for the sustainable and complete exploitation of apple seeds as valuable agro-industrial byproducts, in particular as a rich source of phloridzin and antioxidant flavanols.

Exploratory Characterization of Phenolic Compounds with Demonstrated Anti-Diabetic Activity in Guava Leaves at Different Oxidation States

PubMed Central

Díaz-de-Cerio, Elixabet; Verardo, Vito; Gómez-Caravaca, Ana María; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-01-01

Psidium guajava L. is widely used like food and in folk medicine all around the world. Many studies have demonstrated that guava leaves have anti-hyperglycemic and anti-hyperlipidemic activities, among others, and that these activities belong mainly to phenolic compounds, although it is known that phenolic composition in guava tree varies throughout seasonal changes. Andalusia is one of the regions in Europe where guava is grown, thus, the aim of this work was to study the phenolic compounds present in Andalusian guava leaves at different oxidation states (low, medium, and high). The phenolic compounds in guava leaves were determined by HPLC-DAD-ESI-QTOF-MS. The results obtained by chromatographic analysis reported that guava leaves with low degree of oxidation had a higher content of flavonols, gallic, and ellagic derivatives compared to the other two guava leaf samples. Contrary, high oxidation state guava leaves reported the highest content of cyanidin-glucoside that was 2.6 and 15 times higher than guava leaves with medium and low oxidation state, respectively. The QTOF platform permitted the determination of several phenolic compounds with anti-diabetic properties and provided new information about guava leaf phenolic composition that could be useful for nutraceutical production. PMID:27187352

Exploratory Characterization of Phenolic Compounds with Demonstrated Anti-Diabetic Activity in Guava Leaves at Different Oxidation States.

PubMed

Díaz-de-Cerio, Elixabet; Verardo, Vito; Gómez-Caravaca, Ana María; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-05-11

Psidium guajava L. is widely used like food and in folk medicine all around the world. Many studies have demonstrated that guava leaves have anti-hyperglycemic and anti-hyperlipidemic activities, among others, and that these activities belong mainly to phenolic compounds, although it is known that phenolic composition in guava tree varies throughout seasonal changes. Andalusia is one of the regions in Europe where guava is grown, thus, the aim of this work was to study the phenolic compounds present in Andalusian guava leaves at different oxidation states (low, medium, and high). The phenolic compounds in guava leaves were determined by HPLC-DAD-ESI-QTOF-MS. The results obtained by chromatographic analysis reported that guava leaves with low degree of oxidation had a higher content of flavonols, gallic, and ellagic derivatives compared to the other two guava leaf samples. Contrary, high oxidation state guava leaves reported the highest content of cyanidin-glucoside that was 2.6 and 15 times higher than guava leaves with medium and low oxidation state, respectively. The QTOF platform permitted the determination of several phenolic compounds with anti-diabetic properties and provided new information about guava leaf phenolic composition that could be useful for nutraceutical production.

[Characteristics of the composition of Caucasian blackberry (Rubus caucasicus L.) leaves as a raw material for tea production].

PubMed

Melkadze, R G; Chichkovani, N Sh; Kakhniashvili, E Z

2008-01-01

The composition of Caucasian blackberry (Rubus caucasicus L.) six-leaf shoot was studied. The weight of the stem reached 50% of the total weight of the shoot. The content of moisture, extractive substances, and phenolic compounds was minimal at the beginning and end of the vegetation season. Phenolic compounds were represented by catechins, leukoanthocyanidins, and flavonols. The most abundant phenolic compounds in all parts of the blackberry shoot were leukoanthocyanidins, which accounted for approximately 50% of all compounds of this class. Phenolic compounds accumulated most actively in July and August. The average content of free amino acids in the blackberry leaf during the vegetation season was 26.68 mg/g. Among the total free amino acids, eleven have been identified, five of which proved to be essential (His, Arg, Met, Leu, Val) and accounted for 40% of the total amount of amino acids. The oxidability of acetone extract of the blackberry leaf was compared to the oxidability of total phenolic compounds and tea tannin. The tea product obtained from the blackberry leaf had good organoleptic parameters and a saturated extractive complex.

Identification of Catechin, Syringic Acid, and Procyanidin B2 in Wine as Stimulants of Gastric Acid Secretion.

PubMed

Liszt, Kathrin Ingrid; Eder, Reinhard; Wendelin, Sylvia; Somoza, Veronika

2015-09-09

Organic acids of wine, in addition to ethanol, have been identified as stimulants of gastric acid secretion. This study characterized the influence of other wine compounds, particularly phenolic compounds, on proton secretion. Forty wine parameters were determined in four red wines and six white wines, including the contents of organic acids and phenolic compounds. The secretory activity of the wines was determined in a gastric cell culture model (HGT-1 cells) by means of a pH-sensitive fluorescent dye. Red wines stimulated proton secretion more than white wines. Lactic acid and the phenolic compounds syringic acid, catechin, and procyanidin B2 stimulated proton secretion and correlated with the pro-secretory effect of the wines. Addition of the phenolic compounds to the least active white wine sample enhanced its proton secretory effect by 65 ± 21% (p < 0.05). These results indicate that not only malic and lactic acid but also bitter and astringent tasting phenolic compounds in wine contribute to its stimulatory effect on gastric acid secretion.

Pistachio oil (Pistacia vera L. cv. Uzun): Characterization of key odorants in a representative aromatic extract by GC-MS-olfactometry and phenolic profile by LC-ESI-MS/MS.

PubMed

Sonmezdag, Ahmet Salih; Kelebek, Hasim; Selli, Serkan

2018-02-01

Volatile, aroma-active, and phenolic compounds of pistachio oil obtained from cv. Uzun were investigated in the current study. To obtain a representative aromatic extract, three of the most widely used extraction methods were compared using a representative test; the solvent-assisted flavour extraction (SAFE) aromatic extract from pistachio oil was found to be the most representative. A total of 50 aroma compounds were determined in pistachio oil and it was found that terpenes, aldehydes, and alcohols were the most abundant volatile compounds. Applying GC-MS-olfactometry and aroma extract dilution analysis (AEDA) resulted in a total of 14 aroma-active areas being detected in the extract of pistachio oil. In the phenolic fraction obtained by the LC-ESI-MS/MS method, a total of 12 phenolic compounds was found in the pistachio oil, of which seven compounds were reported for the first time. Eriodictyol-7-O-glucoside and protocatechuic acid were the most dominant phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Effects of Vinification Techniques Combined with UV-C Irradiation on Phenolic Contents of Red Wines.

PubMed

Tahmaz, Hande; Söylemezoğlu, Gökhan

2017-06-01

Red wines are typically high in phenolic and antioxidant capacity and both of which can be increased by vinification techniques. This study employed 3 vinification techniques to assess the increase in phenolic compounds and antioxidant capacity. Wines were obtained from Boğazkere grape cultivar by techniques of classical maceration, cold maceration combined with ultraviolet light (UV) irradiation, and thermovinification combined with UV irradiation and changes in phenolic contents were examined. Total phenolic and anthocyanin contents and trolox equivalent antioxidant capacity of wines were measured spectrophotometrically and phenolic contents (+)-catechin, (-)-epicatechin, rutin, quercetin, trans-resveratrol, and cis-resveratrol were measured by High Pressure Liquid Chromatography with Diode Array Detection (HPLC-DAD). As a result of the study, the highest phenolic content except for quercetin was measured in the wines obtained by thermovinification combined with UV irradiation. We demonstrated that the highest phenolic compounds with health effect, total phenolic compounds, total anthocyanin, and antioxidant activity were obtained from thermovinification with UV-C treatment than classical wine making. © 2017 Institute of Food Technologists®.

The impact of drying techniques on phenolic compound, total phenolic content and antioxidant capacity of oat flour tarhana.

PubMed

Değirmencioğlu, Nurcan; Gürbüz, Ozan; Herken, Emine Nur; Yıldız, Aysun Yurdunuseven

2016-03-01

In this study, the changes in phenolic composition, total phenolic content, and antioxidant capacity of tarhanas supplemented with oat flour (OF) at the levels of 20-100% (w/w) after three drying treatments (sun-, oven-, and microwave drying) were investigated. A total of seventeen phenolic standards have been screened in tarhanas, and the most abundant flavonol and phenolic acid compounds were kaempferol (23.62mg/g) and 3-hydroxy-4-metoxy cinnamic acid (9.60mg/g). The total phenolic content amount gradually increased with the addition of OF to tarhana, but decidedly higher total phenolic content was found in samples oven dried at 55°C as compared with other methods. The microwave- and oven dried tarhana samples showed higher TEACDPPH and TEACABTS values than those dried with the other methods, respectively, in higher OF amounts. Consequently, oven- and microwave-drying can be recommended to retain the highest for phenolic compounds as well as maximal antioxidant capacity in OF supplemented tarhana samples. Copyright © 2015 Elsevier Ltd. All rights reserved.

Enzymatic electrochemical detection coupled to multivariate calibration for the determination of phenolic compounds in environmental samples.

PubMed

Hernandez, Silvia R; Kergaravat, Silvina V; Pividori, Maria Isabel

2013-03-15

An approach based on the electrochemical detection of the horseradish peroxidase enzymatic reaction by means of square wave voltammetry was developed for the determination of phenolic compounds in environmental samples. First, a systematic optimization procedure of three factors involved in the enzymatic reaction was carried out using response surface methodology through a central composite design. Second, the enzymatic electrochemical detection coupled with a multivariate calibration method based in the partial least-squares technique was optimized for the determination of a mixture of five phenolic compounds, i.e. phenol, p-aminophenol, p-chlorophenol, hydroquinone and pyrocatechol. The calibration and validation sets were built and assessed. In the calibration model, the LODs for phenolic compounds oscillated from 0.6 to 1.4 × 10(-6) mol L(-1). Recoveries for prediction samples were higher than 85%. These compounds were analyzed simultaneously in spiked samples and in water samples collected close to tanneries and landfills. Published by Elsevier B.V.

Evaluation of the effect of germination on phenolic compounds and antioxidant activities in sorghum varieties.

PubMed

Dicko, Mamoudou H; Gruppen, Harry; Traore, Alfred S; van Berkel, Willem J H; Voragen, Alphons G J

2005-04-06

The screening of 50 sorghum varieties showed that, on average, germination did not affect the content in total phenolic compounds but decreased the content of proanthocyanidins, 3-deoxyanthocyanidins, and flavan-4-ols. Independent of germination, there are intervarietal differences in antioxidant activities among sorghum varieties. Phenolic compounds and antioxidant activities were more positively correlated in ungerminated varieties than in germinated ones. Sorghum grains with pigmented testa layer, chestnut color glumes, and red plants had higher contents, larger diversity of phenolic compounds, and higher antioxidant activities than other sorghums. Some red sorghum varieties had higher antioxidant activities (30-80 mumol of Trolox equiv/g) than several sources of natural antioxidants from plant foods. Among varieties used for "to", "dolo", couscous, and porridge preparation, the "dolo"(local beer) varieties had the highest average content and diversity in phenolic compounds as well as the highest antioxidant activities. The biochemical markers determined are useful indicators for the selection of sorghum varieties for food and agronomic properties.

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

PubMed Central

Nguyen Thai, Huynh; Van Camp, John; Smagghe, Guy; Raes, Katleen

2014-01-01

This paper provides an overview on steered fermentation processes to release phenolic compounds from plant-based matrices, as well as on their potential application to convert phenolic compounds into unique metabolites. The ability of fermentation to improve the yield and to change the profile of phenolic compounds is mainly due to the release of bound phenolic compounds, as a consequence of the degradation of the cell wall structure by microbial enzymes produced during fermentation. Moreover, the microbial metabolism of phenolic compounds results in a large array of new metabolites through different bioconversion pathways such as glycosylation, deglycosylation, ring cleavage, methylation, glucuronidation and sulfate conjugation, depending on the microbial strains and substrates used. A whole range of metabolites is produced, however metabolic pathways related to the formation and bioactivities, and often quantification of the metabolites are highly underinvestigated. This strategy could have potential to produce extracts with a high-added value from plant-based matrices. PMID:25347275

Degradation of phenolic compounds by the lignocellulose deconstructing thermoacidophilic bacterium Alicyclobacillus Acidocaldarius

DOE PAGES

Aston, John E.; Apel, William A.; Lee, Brady D.; ...

2015-11-05

Alicyclobacillus acidocaldarius, a thermoacidophilic bacterium, has a repertoire of thermo- and acid-stable enzymes that deconstruct lignocellulosic compounds. The work presented here describes the ability of A. acidocaldarius to reduce the concentration of the phenolic compounds: phenol, ferulic acid, ρ-coumaric acid and sinapinic acid during growth conditions. The extent and rate of the removal of these compounds were significantly increased by the presence of micro-molar copper concentrations, suggesting activity by copper oxidases that have been identified in the genome of A. acidocaldarius. Substrate removal kinetics was first order for phenol, ferulic acid, ρ-coumaric acid and sinapinic acid in the presence ofmore » 50 μM copper sulfate. In addition, laccase enzyme assays of cellular protein fractions suggested significant activity on a lignin analog between the temperatures of 45 and 90 °C. As a result, this work shows the potential for A. acidocaldarius to degrade phenolic compounds, demonstrating potential relevance to biofuel production and other industrial processes.« less

Selected phenolic compounds in cultivated plants: ecologic functions, health implications, and modulation by pesticides.

PubMed Central

Daniel, O; Meier, M S; Schlatter, J; Frischknecht, P

1999-01-01

Phenolic compounds are widely distributed in the plant kingdom. Plant tissues may contain up to several grams per kilogram. External stimuli such as microbial infections, ultraviolet radiation, and chemical stressors induce their synthesis. The phenolic compounds resveratrol, flavonoids, and furanocoumarins have many ecologic functions and affect human health. Ecologic functions include defense against microbial pathogens and herbivorous animals. Phenolic compounds may have both beneficial and toxic effects on human health. Effects on low-density lipoproteins and aggregation of platelets are beneficial because they reduce the risk of coronary heart disease. Mutagenic, cancerogenic, and phototoxic effects are risk factors of human health. The synthesis of phenolic compounds in plants can be modulated by the application of herbicides and, to a lesser extent, insecticides and fungicides. The effects on ecosystem functioning and human health are complex and cannot be predicted with great certainty. The consequences of the combined natural and pesticide-induced modulating effects for ecologic functions and human health should be further evaluated. PMID:10229712

Phenolic Compounds of Pomegranate Byproducts (Outer Skin, Mesocarp, Divider Membrane) and Their Antioxidant Activities.

PubMed

Ambigaipalan, Priyatharini; de Camargo, Adriano Costa; Shahidi, Fereidoon

2016-08-31

Pomegranate peel was separated into outer leathery skin (PS), mesocarp (PM), and divider membrane (PD), and its phenolic compounds were extracted as free (F), esterified (E), and insoluble-bound (B) forms for the first time. The total phenolic content followed the order PD > PM > PS. ABTS(•+), DPPH, and hydroxyl radical scavenging activities and metal chelation were evaluated. In addition, pomegranate peel extracts showed inhibitory effects against α-glucosidase activity, lipase activity, and cupric ion-induced LDL-cholesterol oxidation as well as peroxyl and hydroxyl radical-induced DNA scission. Seventy-nine phenolic compounds were identified using HPLC-DAD-ESI-MS(n) mainly in the form of insoluble-bound. Thirty compounds were identified for the first time. Gallic acid was the major phenolic compound in pomegranate peel, whereas kaempferol 3-O-glucoside was the major flavonoid. Moreover, ellagic acid and monogalloyl-hexoside were the major hydrolyzable tannins, whereas the dominant proanthocyanidin was procyanidin dimers. Proanthocyanidins were detected for the first time.

Expression and characteristics of manganese peroxidase from Ganoderma lucidum in Pichia pastoris and its application in the degradation of four dyes and phenol.

PubMed

Xu, Hui; Guo, Meng-Yuan; Gao, Yan-Hua; Bai, Xiao-Hui; Zhou, Xuan-Wei

2017-02-23

Manganese peroxidase (MnP) of white rot basidiomycetes, an extracellular heme enzyme, is part of a peroxidase superfamily that is capable of degrading the different phenolic compounds. Ganoderma, a white rot basidiomycete widely distributed worldwide, could secrete lignin-modifying enzymes (LME), including laccase (Lac), lignin peroxidases (LiP) and MnP. After the selection of a G. lucidum strain from five Ganoderma strains, the 1092 bp full-length cDNA of the MnP gene, designated as G. lucidum MnP (GluMnP1), was cloned from the selected strain. We subsequently constructed an eukaryotic expression vector, pAO815:: GlMnP, and transferred it into Pichia pastoris SMD116. Recombinant GluMnP1 (rGluMnP1) was with a yield of 126 mg/L and a molecular weight of approximately 37.72 kDa and a specific enzyme activity of 524.61 U/L. The rGluMnP1 could be capable of the decolorization of four types of dyes and the degradation of phenol. Phenol and its principal degradation products including hydroquinone, pyrocatechol, resorcinol, benzoquinone, were detected successfully in the experiments. The rGluMnP1 could be effectively expressed in Pichia pastoris and with a higher oxidation activity. We infer that, in the initial stages of the reaction, the catechol-mediated cycle should be the principal route of enzymatic degradation of phenol and its oxidation products. This study highlights the potential industrial applications associated with the production of MnP by genetic engineering methods, and the application of industrial wastewater treatment.

Discovery of New Classes of Compounds that Reactivate Acetylcholinesterase Inhibited by Organophosphates

DOE Office of Scientific and Technical Information (OSTI.GOV)

Katz, Francine S.; Pecic, Stevan; Tran, Timothy H.

Acetylcholinesterase (AChE) that has been covalently inhibited by organophosphate compounds (OPCs), such as nerve agents and pesticides, has traditionally been reactivated by using nucleophilic oximes. There is, however, a clearly recognized need for new classes of compounds with the ability to reactivate inhibited AChE with improved in vivo efficacy. Here we describe our discovery of new functional groups—Mannich phenols and general bases—that are capable of reactivating OPC-inhibited AChE more efficiently than standard oximes and we describe the cooperative mechanism by which these functionalities are delivered to the active site. These discoveries, supported by preliminary in vivo results and crystallographic data,more » significantly broaden the available approaches for reactivation of AChE.« less

Iron deficiency enhances bioactive phenolics in lemon juice.

PubMed

Mellisho, Carmen D; González-Barrio, Rocío; Ferreres, Federico; Ortuño, María F; Conejero, Wenceslao; Torrecillas, Arturo; García-Mina, José M; Medina, Sonia; Gil-Izquierdo, Angel

2011-09-01

This study was designed to describe the phenolic status of lemon juice obtained from fruits of lemon trees differing in iron (Fe) nutritional status. Three types of Fe(III) compound were used in the experiment, namely a synthetic chelate and two complexes derived from natural polymers of humic and lignine nature. All three Fe(III) compounds were able to improve the Fe nutritional status of lemon trees, though to different degrees. This Fe(III) compound effect led to changes in the polyphenol content of lemon juice. Total phenolics were decreased (∼33% average decrease) and, in particular, flavanones, flavones and flavonols were affected similarly. Iron-deficient trees showed higher phenolic contents than Fe(III) compound-treated trees, though Fe deficiency had negative effects on the yield and visual quality of fruits. However, from a human nutritional point of view and owing to the health-beneficial properties of their bioavailable phenolic compounds, the nutritional quality of fruits of Fe-deficient lemon trees in terms of phenolics was higher than that of fruits of Fe(III) compound-treated lemon trees. Moreover, diosmetin-6,8-di-C-glucoside in lemon juice can be used as a marker for correction of Fe deficiency in lemon trees. Copyright © 2011 Society of Chemical Industry.

Ultra‐high performance supercritical fluid chromatography of lignin‐derived phenols from alkaline cupric oxide oxidation

PubMed Central

Sun, Mingzhe; Lidén, Gunnar; Sandahl, Margareta

2016-01-01

Traditional chromatographic methods for the analysis of lignin‐derived phenolic compounds in environmental samples are generally time consuming. In this work, an ultra‐high performance supercritical fluid chromatography method with a diode array detector for the analysis of major lignin‐derived phenolic compounds produced by alkaline cupric oxide oxidation was developed. In an analysis of a collection of 11 representative monomeric lignin phenolic compounds, all compounds were clearly separated within 6 min with excellent peak shapes, with a limit of detection of 0.5–2.5 μM, a limit of quantification of 2.5–5.0 μM, and a dynamic range of 5.0–2.0 mM (R 2 > 0.997). The new ultra‐high performance supercritical fluid chromatography method was also applied for the qualitative and quantitative analysis of lignin‐derived phenolic compounds obtained upon alkaline cupric oxide oxidation of a commercial humic acid. Ten out of the previous eleven model compounds could be quantified in the oxidized humic acid sample. The high separation power and short analysis time obtained demonstrate for the first time that supercritical fluid chromatography is a fast and reliable technique for the analysis of lignin‐derived phenols in complex environmental samples. PMID:27452148

Optimization of Ultrasound Assisted Extraction of Functional Ingredients from Stevia Rebaudiana Bertoni Leaves

NASA Astrophysics Data System (ADS)

Šic Žlabur, Jana; Voća, Sandra; Dobričević, Nadica; Brnčić, Mladen; Dujmić, Filip; Rimac Brnčić, Suzana

2015-04-01

The aim of the present study was to reveal an effective extraction procedure for maximization of the yield of steviol glycosides and total phenolic compounds as well as antioxidant activity in stevia extracts. Ultrasound assisted extraction was compared with conventional solvent extraction. The examined solvents were water (100°C/24 h) and 70% ethanol (at 70°C for 30 min). Qualitative and quantitative analyses of steviol glycosides in the extracts obtained were performed using high performance liquid chromatography. Total phenolic compounds, flavonoids, and radical scavenging capacity by 2, 2-azino-di-3-ethylbenzothialozine- sulphonic acid) assay were also determined. The highest content of steviol glycosides, total phenolic compounds, and flavonoids in stevia extracts were obtained when ultrasound assisted extraction was used. The antioxidant activity of the extracts was correlated with the total amount of phenolic compounds. The results indicated that the examined sonication parameters represented as the probe diameter (7 and 22 mm) and treatment time (2, 4, 6, 8, and 10 min) significantly contributed to the yield of steviol glycosides, total phenolic compounds, and flavonoids. The optimum conditions for the maximum yield of steviol glycosides, total phenolic compounds, and flavonoids were as follows: extraction time 10 min, probe diameter 22 mm, and temperature 81.2°C.

An Overview of Plant Phenolic Compounds and Their Importance in Human Nutrition and Management of Type 2 Diabetes.

PubMed

Lin, Derong; Xiao, Mengshi; Zhao, Jingjing; Li, Zhuohao; Xing, Baoshan; Li, Xindan; Kong, Maozhu; Li, Liangyu; Zhang, Qing; Liu, Yaowen; Chen, Hong; Qin, Wen; Wu, Hejun; Chen, Saiyan

2016-10-15

In this paper, the biosynthesis process of phenolic compounds in plants is summarized, which include the shikimate, pentose phosphate and phenylpropanoid pathways. Plant phenolic compounds can act as antioxidants, structural polymers (lignin), attractants (flavonoids and carotenoids), UV screens (flavonoids), signal compounds (salicylic acid, flavonoids) and defense response chemicals (tannins, phytoalexins). From a human physiological standpoint, phenolic compounds are vital in defense responses, such as anti-aging, anti-inflammatory, antioxidant and anti-proliferative activities. Therefore, it is beneficial to eat such plant foods that have a high antioxidant compound content, which will cut down the incidence of certain chronic diseases, for instance diabetes, cancers and cardiovascular diseases, through the management of oxidative stress. Furthermore, berries and other fruits with low-amylase and high-glucosidase inhibitory activities could be thought of as candidate food items in the control of the early stages of hyperglycemia associated with type 2 diabetes.

Screening plant derived dietary phenolic compounds for bioactivity related to cardiovascular disease.

PubMed

Croft, Kevin D; Yamashita, Yoko; O'Donoghue, Helen; Shirasaya, Daishi; Ward, Natalie C; Ashida, Hitoshi

2018-04-01

The potential health benefits of phenolic acids found in food and beverages has been suggested from a number of large population studies. However, the mechanism of how these compounds may exert biological effects is less well established. It is also now recognised that many complex polyphenols in the diet are metabolised to simple phenolic acids which can be taken up in the circulation. In this paper a number of selected phenolic compounds have been tested for their bioactivity in two cell culture models. The expression and activity of endothelial nitric oxide synthase (eNOS) in human aortic endothelial cells and the uptake of glucose in muscle cells. Our data indicate that while none of the compounds tested had a significant effect on eNOS expression or activation in endothelial cells, several of the compounds increased glucose uptake in muscle cells. These compounds also enhanced the translocation of the glucose transporter GLUT4 to the plasma membrane, which may explain the observed increase in cellular glucose uptake. These results indicate that simple cell culture models may be useful to help understand the bioactivity of phenolic compounds in relation to cardiovascular protection. Copyright © 2017 Elsevier B.V. All rights reserved.

The influence of pH on the degradation of phenol and chlorophenols by potassium ferrate.

PubMed

Graham, Nigel; Jiang, Cheng-Chun; Li, Xiang-Zhong; Jiang, Jia-Qian; Ma, Jun

2004-09-01

This paper presents information concerning the influence of solution pH on the aqueous reaction between potassium ferrate and phenol and three chlorinated phenols: 4-chlorophenol (CP), 2,4-dichlorophenol (DCP), 2,4,6-trichlorophenol (TCP). The redox potential and aqueous stability of the ferrate ion, and the reactivity of dissociating compounds, are known to be pH dependent. Laboratory tests have been undertaken over a wide range of pH (5.8-11) and reactant concentrations (ferrate:compound molar ratios of 1:1 to 8:1). The reactivity of trichloroethylene was also investigated as a reference compound owing to its non-dissociating nature. The extent of compound degradation by ferrate was found to be highly pH dependent, and the optimal pH (maximum degradation) decreased in the order: phenol/CP, DCP, TCP; at the optimal pH the degree of degradation of these compounds was similar. The results indicate that for the group of phenol and chlorophenols studied, the presence of an increasing number of chlorine substituent atoms corresponds to an increasing reactivity of the undissociated compound, and a decreasing reactivity of the dissociated compound.

Is Gamma Radiation Suitable to Preserve Phenolic Compounds and to Decontaminate Mycotoxins in Aromatic Plants? A Case-Study with Aloysia citrodora Paláu.

PubMed

Pereira, Eliana; Barros, Lillian; Antonio, Amilcar L; Cabo Verde, Sandra; Santos-Buelga, Celestino; Ferreira, Isabel C F R; Rodrigues, Paula

2017-02-23

This study aimed to determine the effect of gamma radiation on the preservation of phenolic compounds and on decontamination of dry herbs in terms of ochratoxin A (OTA) and aflatoxin B1 (AFB1), using Aloysia citrodora Paláu as a case study. For this purpose, artificially contaminated dry leaves were submitted to gamma radiation at different doses (1, 5, and 10 kGy; at dose rate of 1.7 kGy/h). Phenolic compounds were analysed by HPLC-DAD-ESI/MS and mycotoxin levels were determined by HPLC-fluorescence. Eleven phenolic compounds were identified in the samples and despite the apparent degradation of some compounds (namely verbasoside), 1 and 10 kGy doses point to a preservation of the majority of the compounds. The mean mycotoxin reduction varied between 5.3% and 9.6% for OTA and from 4.9% to 5.2% for AFB1. It was not observed a significant effect of the irradiation treatments on mycotoxin levels, and a slight degradation of the phenolic compounds in the irradiated samples was observed.

Phenolic compounds as indicators of drought resistance in shrubs from Patagonian shrublands (Argentina).

PubMed

Varela, M Celeste; Arslan, Idris; Reginato, Mariana A; Cenzano, Ana M; Luna, M Virginia

2016-07-01

Plants exposed to drought stress, as usually occurs in Patagonian shrublands, have developed different strategies to avoid or tolerate the lack of water during their development. Production of phenolic compounds (or polyphenols) is one of the strategies used by some native species of adverse environments to avoid the oxidative damage caused by drought. In the present study the relationship between phenolic compounds content, water availability and oxidative damage were evaluated in two native shrubs: Larrea divaricata (evergreen) and Lycium chilense (deciduous) of Patagonian shrublands by their means and/or by multivariate analysis. Samples of both species were collected during the 4 seasons for the term of 1 year. Soil water content, relative water content, total phenols, flavonoids, flavonols, tartaric acid esters, flavan-3-ols, proanthocyanidins, antioxidant capacity and lipid peroxidation were measured. According to statistical univariate analysis, L. divaricata showed high production of polyphenols along the year, with a phenolic compound synthesis enhanced during autumn (season of greatest drought), while L. chilense has lower production of these compounds without variation between seasons. The variation in total phenols along the seasons is proportional to the antioxidant capacity and inversely proportional to lipid peroxidation. Multivariate analysis showed that, regardless their mechanism to face drought (avoidance or tolerance), both shrubs are well adapted to semi-arid regions and the phenolic compounds production is a strategy used by these species living in extreme environments. The identification of polyphenol compounds showed that L. divaricata produces different types of flavonoids, particularly bond with sugars, while L. chilense produces high amount of non-flavonoids compounds. These results suggest that flavonoid production and accumulation could be a useful indicator of drought tolerance in native species. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Olive phenolic compounds: metabolic and transcriptional profiling during fruit development

PubMed Central

2012-01-01

Background Olive (Olea europaea L.) fruits contain numerous secondary metabolites, primarily phenolics, terpenes and sterols, some of which are particularly interesting for their nutraceutical properties. This study will attempt to provide further insight into the profile of olive phenolic compounds during fruit development and to identify the major genetic determinants of phenolic metabolism. Results The concentration of the major phenolic compounds, such as oleuropein, demethyloleuropein, 3–4 DHPEA-EDA, ligstroside, tyrosol, hydroxytyrosol, verbascoside and lignans, were measured in the developing fruits of 12 olive cultivars. The content of these compounds varied significantly among the cultivars and decreased during fruit development and maturation, with some compounds showing specificity for certain cultivars. Thirty-five olive transcripts homologous to genes involved in the pathways of the main secondary metabolites were identified from the massive sequencing data of the olive fruit transcriptome or from cDNA-AFLP analysis. Their mRNA levels were determined using RT-qPCR analysis on fruits of high- and low-phenolic varieties (Coratina and Dolce d’Andria, respectively) during three different fruit developmental stages. A strong correlation was observed between phenolic compound concentrations and transcripts putatively involved in their biosynthesis, suggesting a transcriptional regulation of the corresponding pathways. OeDXS, OeGES, OeGE10H and OeADH, encoding putative 1-deoxy-D-xylulose-5-P synthase, geraniol synthase, geraniol 10-hydroxylase and arogenate dehydrogenase, respectively, were almost exclusively present at 45 days after flowering (DAF), suggesting that these compounds might play a key role in regulating secoiridoid accumulation during fruit development. Conclusions Metabolic and transcriptional profiling led to the identification of some major players putatively involved in biosynthesis of secondary compounds in the olive tree. Our data represent the first step towards the functional characterisation of important genes for the determination of olive fruit quality. PMID:22963618

Metabolism of phenol and hydroquinone to reactive products by macrophage peroxidase or purified prostaglandin H synthase

DOE Office of Scientific and Technical Information (OSTI.GOV)

Schlosser, M.J.; Shurina, R.D.; Kalf, G.F.

1989-07-01

Macrophages, an important cell-type of the bone marrow stroma, are possible targets of benzene toxicity because they contain relatively large amounts of prostaglandin H synthase (PHS), which is capable of metabolizing phenolic compounds to reactive species. PHS also catalyzes the production of prostaglandins, negative regulators of myelopoiesis. Studies indicate that the phenolic metabolites of benzene are oxidized in bone marrow to reactive products via peroxidases. With respect to macrophages, PHS peroxidase is implicated, as in vivo benzene-induced myelotoxicity is prevented by low doses of nonsteroidal anti-inflammatory agents, drugs that inhibit PHS. Incubations of either 14C-phenol or 14C-hydroquinone with a lysatemore » of macrophages collected from mouse peritoneum (greater than 95% macrophages), resulted in an irreversible binding to protein that was dependent upon H2O2, incubation time, and concentration of radiolabel. Production of protein-bound metabolites from phenol or hydroquinone was inhibited by the peroxidase inhibitor aminotriazole. Protein binding from 14C-phenol also was inhibited by 8 microM hydroquinone, whereas binding from 14C-hydroquinone was stimulated by 5 mM phenol. The nucleophile cysteine inhibited protein binding of both phenol and hydroquinone and increased the formation of radiolabeled water-soluble metabolites. Similar to the macrophage lysate, purified PHS also catalyzed the conversion of phenol to metabolites that bound to protein and DNA; this activation was both H2O2- and arachidonic acid-dependent. These results indicate a role for macrophage peroxidase, possibly PHS peroxidase, in the conversion of phenol and hydroquinone to reactive metabolites and suggest that the macrophage should be considered when assessing the hematopoietic toxicity of benzene.« less

Quantification of bioactive compounds in Picual and Arbequina olive leaves and fruit.

PubMed

Romero, Concepción; Medina, Eduardo; Mateo, Mª Antonia; Brenes, Manuel

2017-04-01

Olive leaves and fruit possess bioactive substances such as phenolic compounds and triterpenic acids that can be obtained from olive by-products generated during olive oil extraction. The aim of the present study was the characterization and quantification of these compounds in Picual and Arbequina cultivars from different locations and throughout two seasons in both olive leaves and fruit. The major phenolic compound identified in the leaves was oleuropein, and the total content of phenolic compounds in this material reached 70 g kg -1 fresh weight. The leaves were also rich in triterpenic acids (20 g kg -1 fresh weight), with oleanolic acid being the most concentrated among them. With regard to olives, oleuropein and demethyloleuropein were the main phenolic compounds in the pulp of Picual and Arbequina cultivars, and the total concentration of these phenolic compounds reached 3.5% fresh weight. Olives can also be an important source of triterpenic acids, although this is mainly the skin part, where the maslinic and oleanolic acids are concentrated. Olive leaves can contain up to 70 g kg -1 phenolic compounds and 20 g kg -1 triterpenic acids, and olive fruit can contain up to 35 g kg -1 of the former and 3 g kg -1 of the latter. It must also be noted that this level was constant both between seasons and orchard locations. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

Reductive Dehalogenation of Brominated Phenolic Compounds by Microorganisms Associated with the Marine Sponge Aplysina aerophoba

PubMed Central

Ahn, Young-Beom; Rhee, Sung-Keun; Fennell, Donna E.; Kerkhof, Lee J.; Hentschel, Ute; Häggblom, Max M.

2003-01-01

Marine sponges are natural sources of brominated organic compounds, including bromoindoles, bromophenols, and bromopyrroles, that may comprise up to 12% of the sponge dry weight. Aplysina aerophoba sponges harbor large numbers of bacteria that can amount to 40% of the biomass of the animal. We postulated that there might be mechanisms for microbially mediated degradation of these halogenated chemicals within the sponges. The capability of anaerobic microorganisms associated with the marine sponge to transform haloaromatic compounds was tested under different electron-accepting conditions (i.e., denitrifying, sulfidogenic, and methanogenic). We observed dehalogenation activity of sponge-associated microorganisms with various haloaromatics. 2-Bromo-, 3-bromo-, 4-bromo-, 2,6-dibromo-, and 2,4,6-tribromophenol, and 3,5-dibromo-4-hydroxybenzoate were reductively debrominated under methanogenic and sulfidogenic conditions with no activity observed in the presence of nitrate. Monochlorinated phenols were not transformed over a period of 1 year. Debromination of 2,4,6-tribromophenol, and 2,6-dibromophenol to 2-bromophenol was more rapid than the debromination of the monobrominated phenols. Ampicillin and chloramphenicol inhibited activity, suggesting that dehalogenation was mediated by bacteria. Characterization of the debrominating methanogenic consortia by using terminal restriction fragment length polymorphism (TRFLP) and denaturing gradient gel electrophoresis analysis indicated that different 16S ribosomal DNA (rDNA) phylotypes were enriched on the different halogenated substrates. Sponge-associated microorganisms enriched on organobromine compounds had distinct 16S rDNA TRFLP patterns and were most closely related to the δ subgroup of the proteobacteria. The presence of homologous reductive dehalogenase gene motifs in the sponge-associated microorganisms suggested that reductive dehalogenation might be coupled to dehalorespiration. PMID:12839794

Process for producing phenolic compounds from lignins

DOEpatents

Agblevor, F.A.

1998-09-15

A process is described for the production of low molecular weight phenolic compounds from lignins through the pyrolysis of the lignins in the presence of a strong base. In a preferred embodiment, potassium hydroxide is present in an amount of from about 0.1% to about 5% by weight, the pyrolysis temperature is from about 400 C to about 600 C at atmospheric pressure, and the time period for substantial completion of the reaction is from about 1--3 minutes. Examples of low molecular weight phenolic compounds produced include methoxyphenols, non-methoxylated phenols, and mixtures thereof. 16 figs.

Effect of Low and Very Low Doses of Simple Phenolics on Plant Peroxidase Activity

PubMed Central

Malarczyk, Elżbieta; Kochmańska-Rdest, Janina; Paździoch-Czochra, Marzanna

2004-01-01

Changes in the activity of horseradish peroxidase resulting from an addition of ethanol water dilutions of 19 phenolic compounds were observed. For each compound, the enzyme activity was plotted against the degree of dilution expressed as n = –log100 (mol/L) in the range 0 ≤ n ≥ 20. All the curves showed sinusoidal activity, more or less regular, with two to four peaks on average. Each analyzed compound had a characteristic sinusoidal shape, which was constant for samples of peroxidase from various commercial firms. This was clearly visible after function fitting to experimental results based on the Marquadt–Levenberg algorithm using the least-squares method. Among the 19 phenolics, the highest amplitudes were observed for phenol and iso- and vanillate acids and aldehydes. The specific character of each of the analyzed curves offers a possibility of choosing proper dilutions of phenolic compound for activating or inhibiting of peroxidase activity. PMID:19330128

Phenolic profiles of nectar and honey of Quillaja saponaria Mol. (Quillajaceae) as potential chemical markers.

PubMed

Montenegro, Gloria; Díaz-Forestier, Javiera; Fredes, Carolina; Rodríguez, Sharon

2013-01-01

Quillaja saponaria Mol. (Quillajaceae) is one of the most important melliferous species in Chile, mainly as a source of monofloral honey. Honey made by A. mellifera presents biological activity against pathogens and antioxidant capacity associated with the presence of phenolic compounds deriving from the nectar, as a result of bee honey foraging. The aim of this study was to identify and quantify the phenolic compounds from the floral nectar of Q. saponaria and the honey made in apiaries in the central zone, and compare the composition of the chromatographic profiles of nectar and honey to known phenolic compounds. The results obtained by HPLC-DAD (high-performance liquid chromatography with diode-array detection) showed a similar profile of phenolic compounds, in which gallic acid, myricetin, rutin, quercetin and naringenin were identified. The phenolic compounds detected could be used as a reference for future studies for determining potential chemical markers of this honey, complementing the present identification of honeys by determining their botanical origin. The identification of bioindicators of the floral origins for honey of this species could provide added value to honey commercialization by certifying the botanical origin of their chemical features and biological attributes.

In vitro bioaccessibility, transepithelial transport and antioxidant activity of Urtica dioica L. phenolic compounds in nettle based food products.

PubMed

Bonetti, Gianpiero; Tedeschi, Paola; Meca, Giuseppe; Bertelli, Davide; Mañes, Jordi; Brandolini, Vincenzo; Maietti, Annalisa

2016-10-12

Nettle (Urtica dioica L.) is a well-known plant with a wide historical background use of stems, roots and leaves. Nettle leaves are an excellent source of phenolic compounds, principally 3-caffeoylquinic acid (3-CQA), caffeoylmalic acid (CMA) and rutin. The aim of this work was to evaluate the bioaccessibility (BAC), the bioavailability (BAV) and the antioxidant activity of nettle phenolic compounds present in foods and supplements. The BAC of nettle phenolics was evaluated with an in vitro dynamic digestion of real food matrices: the type of food matrix and chemical characteristic affected the kinetics of release and solubilization, with the highest BAC after duodenal digestion. A study of duodenal trans epithelial transport evidenced low bioavailability of native forms of 3-CQA, CMA and rutin. Simulation of colonic metabolism confirmed that phenolic compounds are fermented by gut microflora, confirming the need for further investigations on the impact of phenolic compounds at the large intestine level. Photochemiluminescence assay of the simulated digestion fluids demonstrated that ingestion of Urtica based foods contributes to create an antioxidant environment against superoxide anion radicals in the entire gastrointestinal tract (GIT).

Reducing the allergenic capacity of peanut extracts and liquid peanut butter by phenolic compounds.

USDA-ARS?s Scientific Manuscript database

Phenolic compounds are known to form soluble and insoluble complexes with proteins. The objective of this study was to determine if phenolics, such as, caffeic, chlorogenic, and ferulic acids form insoluble and irreversible complexes with major peanut allergens. We also tested whether such complexat...

Dynamics in the concentrations of health-promoting compounds: lupeol, mangiferin and different phenolic acids during postharvest ripening of mango fruit.

PubMed

Vithana, Mekhala Dk; Singh, Zora; Johnson, Stuart K

2018-03-01

Mango fruit (Mangifera indica L.) is renowned for its pleasant taste and as a rich source of health beneficial compounds. The aim of this study was to investigate the changes in concentrations of health-promoting compounds, namely ascorbic acid, carotenoids, antioxidants, lupeol, mangiferin, total phenols and individual phenolic acids, as well as ethylene production and respiration rates during climacteric ripening in 'Kensington Pride' and 'R2E2' mango fruit. The climacteric ethylene and respiration peaks were noted on the third day of the fruit ripening period. The concentrations of total carotenoids in the pulp, total antioxidants in both pulp and peel, and total phenols of the peel, lupeol and mangiferin were significantly elevated, whereas the concentration of ascorbic acid declined during post-climacteric ripening. Gallic, chlorogenic and vanillic acids were identified as the major phenolic acids in both pulp and peel of 'Kensington Pride' and 'R2E2' mangoes. The concentrations of phenolic acids (gallic, chlorogenic, vanillic, ferulic and caffeic acids) also increased during the post-climacteric phase. The concentrations of all phenolic compounds were several-fold higher in the peel than pulp. Mangoes at post-climacteric ripening phase offer the highest concentrations of health-promoting compounds. Peel, at this stage of fruit ripening, could be exploited as a good source for extraction of these compounds. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Bioremediation of phenolic compounds from water with plant root surface peroxidases

DOE Office of Scientific and Technical Information (OSTI.GOV)

Adler, P.R.; Arora, R.; El Ghaouth, A.

1994-09-01

Peroxidases have been shown to polymerize phenolic compounds, thereby removing them from solution by precipitation. Others have studied the role of root surface associated peroxidases as a defense against fungal root pathogens; however, their use in detoxification of organic pollutants in vivo at the root surface has not been studied. Two plant species, waterhyacinth [Eichhornia crassipes (C. Mart) Solms-Laub.] and tomato (Lycopersicon esculentum L.), were tested for both in vitro and in vivo peroxidase activity on the root surface. In vitro studies indicated that root surface peroxidase activities were 181 and 78 nmol tetraguaiacol formed min{sup -1} g{sup -1} rootmore » fresh wt., for tomato and waterhyacinth, respectively. Light microscope studies revealed that guaiacol was polymerized in vivo at the root surface. Although peroxidase was evenly distributed on tomato roots, it was distributed patchily on waterhyacinth roots. In vitro studies using gas chromatography-mass spectrometry (GC-MS) showed that the efficiency of peroxidase to polymerize phenols vary with phenolic compound. We suggest that plants may be utilized as a source of peroxidases for removal of phenolic compounds that are on the EPA priority pollutant list and that root surface peroxidases may minimize the absorption of phenolic compounds into plants by precipitating them at the root surface. In this study we have identified a new use for root-associated proteins in ecologically engineering plant systems for bioremediation of phenolic compounds in the soil and water environment. 25 refs., 2 figs., 2 tabs.« less

Partition behavior of virgin olive oil phenolic compounds in oil-brine mixtures during thermal processing for fish canning.

PubMed

Sacchi, Raffaele; Paduano, Antonello; Fiore, Francesca; Della Medaglia, Dorotea; Ambrosino, Maria Luisa; Medina, Isabel

2002-05-08

The chemical modifications and partitioning toward the brine phase (5% salt) of major phenol compounds of extra virgin olive oil (EVOO) were studied in a model system formed by sealed cans filled with oil-brine mixtures (5:1, v/v) simulating canned-in-oil food systems. Filled cans were processed in an industrial plant using two sterilization conditions commonly used during fish canning. The partitioning of phenolic compounds toward brine induced by thermal processing was studied by reversed-phase high-performance liquid chromatographic analysis of the phenol fraction extracted from oils and brine. Hydroxytyrosol (1), tyrosol (2), and the complex phenolic compounds containing 1 and 2 (i.e., the dialdehydic form of decarboxymethyl oleuropein aglycon 3, the dialdehydic form of decarboxymethyl ligstroside aglycon 4, and the oleuropein aglycon 6) decreased in the oily phase after sterilization with a marked partitioning toward the brine phase. The increase of the total amount of 1 and 2 after processing, as well as the presence of elenolic acid 7 released in brine, revealed the hydrolysis of the ester bond of hydrolyzable phenolic compounds 3, 4, and 6 during thermal processing. Both phenomena (partitioning toward the water phase and hydrolysis) contribute to explain the loss of phenolic compounds exhibited by EVOO used as filling medium in canned foods, as well as the protection of n-3 polyunsaturated fatty acids in canned-in-EVOO fish products.

Spectrophotometric Determination of Phenolic Antioxidants in the Presence of Thiols and Proteins.

PubMed

Avan, Aslı Neslihan; Demirci Çekiç, Sema; Uzunboy, Seda; Apak, Reşat

2016-08-12

Development of easy, practical, and low-cost spectrophotometric methods is required for the selective determination of phenolic antioxidants in the presence of other similar substances. As electron transfer (ET)-based total antioxidant capacity (TAC) assays generally measure the reducing ability of antioxidant compounds, thiols and phenols cannot be differentiated since they are both responsive to the probe reagent. In this study, three of the most common TAC determination methods, namely cupric ion reducing antioxidant capacity (CUPRAC), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt/trolox equivalent antioxidant capacity (ABTS/TEAC), and ferric reducing antioxidant power (FRAP), were tested for the assay of phenolics in the presence of selected thiol and protein compounds. Although the FRAP method is almost non-responsive to thiol compounds individually, surprising overoxidations with large positive deviations from additivity were observed when using this method for (phenols + thiols) mixtures. Among the tested TAC methods, CUPRAC gave the most additive results for all studied (phenol + thiol) and (phenol + protein) mixtures with minimal relative error. As ABTS/TEAC and FRAP methods gave small and large deviations, respectively, from additivity of absorbances arising from these components in mixtures, mercury(II) compounds were added to stabilize the thiol components in the form of Hg(II)-thiol complexes so as to enable selective spectrophotometric determination of phenolic components. This error compensation was most efficient for the FRAP method in testing (thiols + phenols) mixtures.

Phenolic Compounds in Particles of Mainstream Waterpipe Smoke

PubMed Central

2013-01-01

Introduction: Waterpipe tobacco smoking has in recent years become a popular international phenomenon, particularly among youth. While it has been shown to deliver significant quantities of several carcinogenic and toxic substances, phenols, an important class of chemical compounds thought to promote DNA mutation and cardiovascular diseases, however, has not been studied. Due to the relatively low temperature characteristic of waterpipe tobacco during smoking (i.e., <450 °C), it was hypothesized that phenolic compounds, which form at approximately 300 °C, will be found in abundance in waterpipe smoke. Methods: In this study, phenolic compounds in the particle phase of waterpipe mainstream smoke were quantified. Waterpipe and cigarette mainstream smoke generated using standard methods were collected on glass fiber pads and analyzed using gas chromatography/mass spectroscopy selected ion current profile chromatogram method for quantification. Results: We found that relative to a single cigarette, a waterpipe delivers at least 3 times greater quantities of the 7 analyzed phenols (phenol, o-cresol, m-cresol, p-cresol, catechol, resorcinol, and hydroquinone). Moreover, phenol derivatives such as methylcatechol, and flavorings such as vanillin, ethyl vanillin, and benzyl alcohol were found in quantities up to 1,000 times greater than the amount measured in the smoke of a single cigarette. Conclusion: The large quantities of phenols and phenol derivatives in waterpipe smoke add to the growing evidence that habitual waterpipe use may increase the risk of cancer and cardiovascular diseases. PMID:23178319

Rapid profiling of polymeric phenolic acids in Salvia miltiorrhiza by hybrid data-dependent/targeted multistage mass spectrometry acquisition based on expected compounds prediction and fragment ion searching.

PubMed

Shen, Yao; Feng, Zijin; Yang, Min; Zhou, Zhe; Han, Sumei; Hou, Jinjun; Li, Zhenwei; Wu, Wanying; Guo, De-An

2018-04-01

Phenolic acids are the major water-soluble components in Salvia miltiorrhiza (>5%). According to previous studies, many of them contribute to the cardiovascular effects and antioxidant effects of S. miltiorrhiza. Polymeric phenolic acids can be considered as the tanshinol derived metabolites, e.g., dimmers, trimers, and tetramers. A strategy combined with tanshinol-based expected compounds prediction, total ion chromatogram filtering, fragment ion searching, and parent list-based multistage mass spectrometry acquisition by linear trap quadropole-orbitrap Velos mass spectrometry was proposed to rapid profile polymeric phenolic acids in S. miltiorrhiza. More than 480 potential polymeric phenolic acids could be screened out by this strategy. Based on the fragment information obtained by parent list-activated data dependent multistage mass spectrometry acquisition, 190 polymeric phenolic acids were characterized by comparing their mass information with literature data, and 18 of them were firstly detected from S. miltiorrhiza. Seven potential compounds were tentatively characterized as new polymeric phenolic acids from S. miltiorrhiza. This strategy facilitates identification of polymeric phenolic acids in complex matrix with both selectivity and sensitivity, which could be expanded for rapid discovery and identification of compounds from complex matrix. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of the phenolic content, profile, and antioxidant activity of seeds from nine tree peony (Paeonia section Moutan DC.) species native to China.

PubMed

Zhang, Xiao-Xiao; Shi, Qian-Qian; Ji, Duo; Niu, Li-Xin; Zhang, Yan-Long

2017-07-01

As an important resource of functional food, the seeds of tree peony are rich in phenolic compounds, which are associated with antioxidant activity. However, so far there has not been systematic study on phenolic compositions and antioxidant activity of the seeds from wild tree peony species. The aim of this study was to determine the phenolic content, antioxidant compounds and antioxidant activity of seeds from nine tree peony species native to China. Among the seed samples, Paeonia rockii had the highest total flavonoid content, strongest DPPH and ABTS radical scavenging activities, and strongest cupric reducing capacity; P. decomposita subsp. rotundiloba had the highest total phenolic and flavanol contents, as well as the strongest hydroxyl radical scavenging activity. Sixteen individual phenolic compounds were quantitatively measured, with (+)-catechin being the most abundant component. The content of the phenolic compounds luteolin, paeonol, and the total flavonoid content were significantly correlated with four antioxidant activities. Hierarchical cluster analysis showed that P. rockii and P. decomposita subsp. rotundiloba could be clustered in a group having a high phenolic content and strong antioxidant activity. These results suggest P. rockii and P. decomposita subsp. rotundiloba are the most promising candidates as useful sources of natural antioxidants. Copyright © 2017. Published by Elsevier Ltd.

Capillary electrophoresis-electrospray ionization-mass spectrometry method to determine the phenolic fraction of extra-virgin olive oil.

PubMed

Carrasco-Pancorbo, Alegría; Arráez-Román, David; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

2006-06-01

We describe the first analytical method involving SPE and CZE coupled to ESI-IT MS (CZE-ESI-MS) used to identify and characterize phenolic compounds in olive oil samples. The SPE, CZE and ESI-MS parameters were optimized in order to maximize the number of phenolic compounds detected and the sensitivity of their determination. To this end we have devised a detailed method to find the best conditions for CE separation and the detection by MS of the phenolic compounds present in olive oil using a methanol-water extract of Picual extra-virgin olive oil (VOO). Electrophoretic separation was carried out using an aqueous CE buffer system consisting of 60 mM NH(4)OAc at pH 9.5 with 5% of 2-propanol, a sheath liquid containing 2-propanol/water 60:40 v/v and 0.1% v/v triethylamine. This method offers to the analyst the chance to study important phenolic compounds such as phenolic alcohols (tyrosol (TY), hydroxytyrosol (HYTY) and 2-(4-hydroxyphenyl)ethyl acetate), lignans ((+)-pinoresinol and (+)-1-acetoxypinoresinol), complex phenols (ligstroside aglycon (Lig Agl), oleuropein aglycon, their respective decarboxylated derivatives and several isomeric forms of these (dialdehydic form of oleuropein aglycon, dialdehydic form of ligstroside aglycon, dialdehydic form of decarboxymethyl elenolic acid linked to HYTY, dialdehydic form of decarboxymethyl elenolic acid linked to TY) and 10-hydroxy-oleuropein aglycon) and one other phenolic compound (elenolic acid) in extra-VOO by using a simple SPE before CE-ESI-MS analysis.

Antioxidant and antimicrobial activity of natural phenolic extract from defatted soybean flour by-product for stone fruit postharvest application.

PubMed

Villalobos, María del Carmen; Serradilla, Manuel Joaquín; Martín, Alberto; Ordiales, Elena; Ruiz-Moyano, Santiago; Córdoba, María de Guía

2016-04-01

Fresh fruit is highly perishable during storage and transport, so there has been growing interest in finding safe and natural antimicrobial compounds as a control tool. Phenolic compounds are secondary metabolites naturally present in vegetable material and have been associated with antimicrobial and antioxidant properties. Therefore, the aim of this study was to investigate the antioxidant capacity and potential antimicrobial effect of phenolic extract obtained from defatted soybean flour against selected pathogenic bacteria and microorganisms responsible of fruit decay. Analysis of phenolic composition by HPLC-MS showed the presence of a wide range of compounds, with isoflavones and phenolic acids the main polyphenols identified. Furthermore, the phenolic extract had important antioxidant activity by two different assays. Related to antimicrobial activity, in vitro experiments demonstrated that phenolic extract displayed a high activity against the main foodborne pathogens, while a moderate inhibition was found against five spoilage yeasts and Monilia laxa and a scarce effect for Penicillium glabrum, Cladosporium uredinicola and Botrytis cinerea. Interestingly these compounds considerably inhibited the mycelial growth of Monilia laxa, in both in vitro and in vivo experiments. The results of the present study revealed that defatted soybean flour is an important source of phenolic compounds with remarkable antimicrobial and antioxidant activity, suggesting the possibility of using them as natural additives in postharvest treatments to extend the shelf life of fruit. © 2015 Society of Chemical Industry.

Bioactive compounds and quality parameters of natural cloudy lemon juices.

PubMed

Uçan, Filiz; Ağçam, Erdal; Akyildiz, Asiye

2016-03-01

In this study, bioactive compounds (phenolic and carotenoid) and some quality parameters (color, browning index and hydroxymethylfurfural (HMF)) of natural cloudy lemon juice, pasteurized (90 °C/15 s) and storage stability of concentrated lemon juice (-25 °C/180 days) were carried out. Fifteen phenolic compounds were determined in the lemon juice and the most abounded phenolic compounds were hesperidin, eriocitrin, chlorogenic acid and neoeriocitrin. In generally, phenolic compound concentrations of lemon juice samples increased after the pasteurization treatment. Four carotenoid compounds (β-carotene, β-cryptoxanthin, lutein and zeaxanthin) were detected in natural cloudy lemon juice. Lutein and β-cryptoxanthin were the most abounded carotenoid compounds in the lemon juice. Color values of the lemon juices were not affected by processing and storage periods. HMF and browning index of the lemon juices increased with concentration and storage. According to the results, storing at -25 °C was considered as sufficient for acceptable quality limits of natural cloudy lemon juice.

Biochemical changes in phenols, flavonoids, tannins, vitamin E, β-carotene and antioxidant activity during soaking of three white sorghum varieties

PubMed Central

Afify, Abd El-Moneim MR; El-Beltagi, Hossam S; El-Salam, Samiha M Abd; Omran, Azza A

2012-01-01

Objective To investigate the changes in total phenols, flavonoids, tannins, vitamin E, β-carotene and antioxidant activity during soaking of three white sorghum varieties. Methods The changes in total phenols, total flavonoids, tannins, phenolic acids compounds, flavonoid components, vitamin E, β-carotene and antioxidant activity during soaking of sorghum grains were determined. Results Total phenols, total flavonoids, tannins, vitamin E, β-carotene and antioxidant activity in raw sorghum were ranged from 109.21 to 116.70, 45.91 to 54.69, 1.39 to 21.79 mg/100 g, 1.74 to 5.25, 0.54 to 1.19 mg/kg and 21.72% to 27.69% and 25.29% to 31.97%, respectively. The above measured compounds were significantly decreased after soaking. p-Hydroxybenzoic acid, vanillic acid, syringic acid and cinnamic acid represent the major phenolic acids in Dorado variety. While ferulic acid, p-coumaric acid, gallic acid and caffeic acid represent the major phenolic acids in Shandaweel-6. On the other hand, protocatechuic acid represents the major phenolic acids in Giza-15. Regarding flavonoids components, Dorado was the highest variety in kampferol and naringenin while Shandaweel-6 was the highest variety in luteolin, apigenin, hypersoid, quercetin and christen. Finally, Giza-15 was the highest variety in catechin. Phenolic acids, flavonoid compounds and antioxidant activities were decreased after soaking. Conclusions Sorghum varieties have moderate quantities from total phenols, total flavonoids, tannins, phenolic acids compounds, flavonoid components, vitamin E, β-carotene and antioxidant activity which decreased after soaking. PMID:23569898

Biochemical changes in phenols, flavonoids, tannins, vitamin E, β-carotene and antioxidant activity during soaking of three white sorghum varieties.

PubMed

Afify, Abd El-Moneim M R; El-Beltagi, Hossam S; El-Salam, Samiha M Abd; Omran, Azza A

2012-03-01

To investigate the changes in total phenols, flavonoids, tannins, vitamin E, β-carotene and antioxidant activity during soaking of three white sorghum varieties. The changes in total phenols, total flavonoids, tannins, phenolic acids compounds, flavonoid components, vitamin E, β-carotene and antioxidant activity during soaking of sorghum grains were determined. Total phenols, total flavonoids, tannins, vitamin E, β-carotene and antioxidant activity in raw sorghum were ranged from 109.21 to 116.70, 45.91 to 54.69, 1.39 to 21.79 mg/100 g, 1.74 to 5.25, 0.54 to 1.19 mg/kg and 21.72% to 27.69% and 25.29% to 31.97%, respectively. The above measured compounds were significantly decreased after soaking. p-Hydroxybenzoic acid, vanillic acid, syringic acid and cinnamic acid represent the major phenolic acids in Dorado variety. While ferulic acid, p-coumaric acid, gallic acid and caffeic acid represent the major phenolic acids in Shandaweel-6. On the other hand, protocatechuic acid represents the major phenolic acids in Giza-15. Regarding flavonoids components, Dorado was the highest variety in kampferol and naringenin while Shandaweel-6 was the highest variety in luteolin, apigenin, hypersoid, quercetin and christen. Finally, Giza-15 was the highest variety in catechin. Phenolic acids, flavonoid compounds and antioxidant activities were decreased after soaking. Sorghum varieties have moderate quantities from total phenols, total flavonoids, tannins, phenolic acids compounds, flavonoid components, vitamin E, β-carotene and antioxidant activity which decreased after soaking.

Use of different spices as potential natural antioxidant additives on cooked beans (Phaseolus vulgaris). Increase of DPPH radical scavenging activity and total phenolic content.

PubMed

Pereira, Marina Pelincer; Tavano, Olga Luisa

2014-12-01

Herbs and spices, excellent sources of phenolic compounds, can be considered potential antioxidant additives. The use of spices must strike a balance between their potential antioxidant capabilities during preparation and the flavor acceptance, in order to avoid rejection of the food. The aimed of this study is to evaluate the influence of different spices and their concentrations on cooked common beans, focusing its potential as antioxidant additives. Onion, parsley, spring onion, laurel and coriander increased the antioxidant activity of preparation when used at 7.96 g of onion, 1.06 g parsley, 3.43 g spring onion, 0.25 g laurel (dry leaves), and 0.43 g coriander/100 g of cooked beans. Besides, these spices concentrations enhance total phenolics and alter the mixture protein digestibility minimally. For garlic samples it was not possible to establish a concentration that increases the antioxidant activity of cooked beans.

Extraction, evolution, and sensory impact of phenolic compounds during red wine maceration.

PubMed

Casassa, L Federico; Harbertson, James F

2014-01-01

We review the extraction into wine and evolution of major phenolic classes of sensory relevance. We present a historical background to highlight that previously established aspects of phenolic extraction and retention into red wine are still subjects of much research. We argue that management of the maceration length is one of the most determining factors in defining the proportion and chemical fate of phenolic compounds in wine. The extraction of anthocyanins, flavonols, flavan-3-ols, and oligomeric and polymeric proanthocyanidins (PAs) is discussed in the context of their individual extraction patterns but also with regard to their interaction with other wine components. The same approach is followed to present the sensory implications of phenolic and phenolic-derived compounds in wine. Overall, we conclude that the chemical diversity of phenolic compounds in grapes is further enhanced as soon as vacuolar and pulp components are released upon crushing, adding a variety of new sensory dimensions to the already present chemical diversity. Polymeric pigments formed by the covalent reaction of anthocyanin and PAs are good candidates to explain some of the observed sensory changes in the color, taste, and mouthfeel attributes of red wines during maceration and aging.

Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation.

PubMed

García-Martínez, Olga; De Luna-Bertos, Elvira; Ramos-Torrecillas, Javier; Ruiz, Concepción; Milia, Egle; Lorenzo, María Luisa; Jimenez, Brigida; Sánchez-Ortiz, Araceli; Rivas, Ana

2016-01-01

In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11-16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18-22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9-13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly.

Changes in element accumulation, phenolic metabolism, and antioxidative enzyme activities in the red-skin roots of Panax ginseng.

PubMed

Zhou, Ying; Yang, Zhenming; Gao, Lingling; Liu, Wen; Liu, Rongkun; Zhao, Junting; You, Jiangfeng

2017-07-01

Red-skin root disease has seriously decreased the quality and production of Panax ginseng (ginseng). To explore the disease's origin, comparative analysis was performed in different parts of the plant, particularly the epidermis, cortex, and/or fibrous roots of 5-yr-old healthy and diseased red-skin ginseng. The inorganic element composition, phenolic compound concentration, reactive oxidation system, antioxidant concentrations such as ascorbate and glutathione, activities of enzymes related to phenolic metabolism and oxidation, and antioxidative system particularly the ascorbate-glutathione cycle were examined using conventional methods. Aluminum (Al), iron (Fe), magnesium, and phosphorus were increased, whereas manganese was unchanged and calcium was decreased in the epidermis and fibrous root of red-skin ginseng, which also contained higher levels of phenolic compounds, higher activities of the phenolic compound-synthesizing enzyme phenylalanine ammonia-lyase and the phenolic compound oxidation-related enzymes guaiacol peroxidase and polyphenoloxidase. As the substrate of guaiacol peroxidase, higher levels of H 2 O 2 and correspondingly higher activities of superoxide dismutase and catalase were found in red-skin ginseng. Increased levels of ascorbate and glutathione; increased activities of l-galactose 1-dehydrogenase, ascorbate peroxidase, ascorbic acid oxidase, and glutathione reductase; and lower activities of dehydroascorbate reductase, monodehydroascorbate reductase, and glutathione peroxidase were found in red-skin ginseng. Glutathione- S -transferase activity remained constant. Hence, higher element accumulation, particularly Al and Fe, activated multiple enzymes related to accumulation of phenolic compounds and their oxidation. This might contribute to red-skin symptoms in ginseng. It is proposed that antioxidant and antioxidative enzymes, especially those involved in ascorbate-glutathione cycles, are activated to protect against phenolic compound oxidation.

Insights into lignin degradation and its potential industrial applications.

PubMed

Abdel-Hamid, Ahmed M; Solbiati, Jose O; Cann, Isaac K O

2013-01-01

Lignocellulose is an abundant biomass that provides an alternative source for the production of renewable fuels and chemicals. The depolymerization of the carbohydrate polymers in lignocellulosic biomass is hindered by lignin, which is recalcitrant to chemical and biological degradation due to its complex chemical structure and linkage heterogeneity. The role of fungi in delignification due to the production of extracellular oxidative enzymes has been studied more extensively than that of bacteria. The two major groups of enzymes that are involved in lignin degradation are heme peroxidases and laccases. Lignin-degrading peroxidases include lignin peroxidase (LiP), manganese peroxidase (MnP), versatile peroxidase (VP), and dye-decolorizing peroxidase (DyP). LiP, MnP, and VP are class II extracellular fungal peroxidases that belong to the plant and microbial peroxidases superfamily. LiPs are strong oxidants with high-redox potential that oxidize the major non-phenolic structures of lignin. MnP is an Mn-dependent enzyme that catalyzes the oxidation of various phenolic substrates but is not capable of oxidizing the more recalcitrant non-phenolic lignin. VP enzymes combine the catalytic activities of both MnP and LiP and are able to oxidize Mn(2+) like MnP, and non-phenolic compounds like LiP. DyPs occur in both fungi and bacteria and are members of a new superfamily of heme peroxidases called DyPs. DyP enzymes oxidize high-redox potential anthraquinone dyes and were recently reported to oxidize lignin model compounds. The second major group of lignin-degrading enzymes, laccases, are found in plants, fungi, and bacteria and belong to the multicopper oxidase superfamily. They catalyze a one-electron oxidation with the concomitant four-electron reduction of molecular oxygen to water. Fungal laccases can oxidize phenolic lignin model compounds and have higher redox potential than bacterial laccases. In the presence of redox mediators, fungal laccases can oxidize non-phenolic lignin model compounds. In addition to the peroxidases and laccases, fungi produce other accessory oxidases such as aryl-alcohol oxidase and the glyoxal oxidase that generate the hydrogen peroxide required by the peroxidases. Lignin-degrading enzymes have attracted the attention for their valuable biotechnological applications especially in the pretreatment of recalcitrant lignocellulosic biomass for biofuel production. The use of lignin-degrading enzymes has been studied in various applications such as paper industry, textile industry, wastewater treatment and the degradation of herbicides. Copyright © 2013 Elsevier Inc. All rights reserved.

Effects of koji fermented phenolic compounds on the oxidative stability of fish miso.

PubMed

Giri, Anupam; Osako, Kazufumi; Okamoto, Akira; Okazaki, Emiko; Ohshima, Toshiaki

2012-02-01

In the present study, Aspergillus oryzae-inoculated koji inhibited lipid oxidation in fermented fish paste rich in polyunsaturated fatty acids following a long fermentation period. The fermentation of koji by A. oryzae liberated several bioactive phenolic compounds, including kojic acid and ferulic acid, which were the most abundant. A linear correlation between several phenolic compounds and their bioactive properties, including their radical-scavenging activity, reducing power, metal-chelating activity, and ability to inhibit linoleic acid oxidation was observed. This suggested an important role of koji phenolics in the oxidative stability of fermented fish paste. The activities of different carbohydrate-cleaving enzymes, including α-amylase, cellulase, and β-glucosidase, were positively correlated with the liberation of several phenolic compounds through koji fermentation. Thus, the application of koji offers a novel strategy to enhance the oxidative stability of newly developed fermented fish miso. Application of traditional Japanese koji fermentation technique to develop an aroma enriched fish meat bases seasoning has been established. Aspergillus oryzae-inoculated koji releases several carbohydrate-cleaving enzymes, including α-amylase, cellulose, and β-glucosidase, which led to the liberation of several phenolic compounds during fermentation. Improvement of oxidative stability of the fermented fish meat paste by koji phenolics suggests a useful strategy to uplift the value of different trash fish meat-based seasoning through proper utilization of the present technique. © 2012 Institute of Food Technologists®

Chemistry and health of olive oil phenolics.

PubMed

Cicerale, Sara; Conlan, Xavier A; Sinclair, Andrew J; Keast, Russell S J

2009-03-01

The Mediterranean diet is associated with a lower incidence of atherosclerosis, cardiovascular disease, and certain types of cancer. The apparent health benefits have been partially attributed to the dietary consumption of virgin olive oil by Mediterranean populations. Most recent interest has focused on the biologically active phenolic compounds naturally present in virgin olive oils. Studies (human, animal, in vivo and in vitro) have shown that olive oil phenolics have positive effects on certain physiological parameters, such as plasma lipoproteins, oxidative damage, inflammatory markers, platelet and cellular function, and antimicrobial activity. Presumably, regular dietary consumption of virgin olive oil containing phenolic compounds manifests in health benefits associated with a Mediterranean diet. This paper summarizes current knowledge on the physiological effects of olive oil phenolics. Moreover, a number of factors have the ability to affect phenolic concentrations in virgin olive oil, so it is of great importance to understand these factors in order to preserve the essential health promoting benefits of olive oil phenolic compounds.

Artificial neural network modelling of the antioxidant activity and phenolic compounds of bananas submitted to different drying treatments.

PubMed

Guiné, Raquel P F; Barroca, Maria João; Gonçalves, Fernando J; Alves, Mariana; Oliveira, Solange; Mendes, Mateus

2015-02-01

Bananas (cv. Musa nana and Musa cavendishii) fresh and dried by hot air at 50 and 70°C and lyophilisation were analysed for phenolic contents and antioxidant activity. All samples were subject to six extractions (three with methanol followed by three with acetone/water solution). The experimental data served to train a neural network adequate to describe the experimental observations for both output variables studied: total phenols and antioxidant activity. The results show that both bananas are similar and air drying decreased total phenols and antioxidant activity for both temperatures, whereas lyophilisation decreased the phenolic content in a lesser extent. Neural network experiments showed that antioxidant activity and phenolic compounds can be predicted accurately from the input variables: banana variety, dryness state and type and order of extract. Drying state and extract order were found to have larger impact in the values of antioxidant activity and phenolic compounds. Copyright © 2014 Elsevier Ltd. All rights reserved.

Bioaccessibility and potential bioavailability of phenolic compounds from achenes as a new target for strawberry breeding programs.

PubMed

Ariza, María Teresa; Reboredo-Rodríguez, Patricia; Cervantes, Lucía; Soria, Carmen; Martínez-Ferri, Elsa; González-Barreiro, Carmen; Cancho-Grande, Beatriz; Battino, Maurizio; Simal-Gándara, Jesús

2018-05-15

Strawberry is a major natural source of bioactive compounds. Botanically, strawberry is an aggregate fruit consisting of a fleshy floral receptacle that bears a cluster of real dry fruits (achenes). Existing knowledge on the phenolic composition of achenes and its contribution to that of the whole fruit is limited. Also, the gastric and intestinal bioavailability of phenols is poorly known. In this work, a combination of spectrophotometric and HPLC-DAD methods was used to analyse the phenolic composition of whole fruits and achenes before and after in vitro digestion. Five different phenol families were identified. Also, achenes were found to contribute a sizeable fraction of phenolic acids and hydrolysable tannins in the whole fruit. Because the mere presence of phenolic compounds in a food matrix does not ensure their ready absorption and bioavailability, polyphenol potential bioavailability could be an effective selection criterion for strawberry breeding programs aimed at improving dietary healthiness. Copyright © 2017 Elsevier Ltd. All rights reserved.

Anaerobic biodegradation of phenolic compounds in digested sludge.

PubMed Central

Boyd, S A; Shelton, D R; Berry, D; Tiedje, J M

1983-01-01

We examined the anaerobic degradation of phenol and the ortho, meta, and para isomers of chlorophenol, methoxyphenol, methylphenol (cresol), and nitrophenol in anaerobic sewage sludge diluted to 10% in a mineral salts medium. Of the 12 monosubstituted phenols studied, only p-chlorophenol and o-cresol were not significantly degraded during an 8-week incubation period. The phenol compounds degraded and the time required for complete substrate disappearance (in weeks) were: phenol (2), o-chlorophenol (3), m-chlorophenol (7), o-methoxyphenol (2), m- and p-methoxyphenol (1), m-cresol (7), p-cresol (3), and o-, m-, and p-nitrophenol (1). Complete mineralization of phenol, o-chlorophenol, m-cresol, p-cresol, o-nitrophenol, p-nitrophenol, and o-, m-, and p-methoxyphenol was observed. In general, the presence of Cl and NO2 groups on phenols inhibited methane production. Elimination or transformation of these substituents was accompanied by increased methane production, o-Chlorophenol was metabolized to phenol, which indicated that dechlorination was the initial degradation step. The methoxyphenols were transformed to the corresponding dihydroxybenzene compounds, which were subsequently mineralized. PMID:6614908

Copper-catalyzed oxidative C-O bond formation of 2-acyl phenols and 1,3-dicarbonyl compounds with ethers: direct access to phenol esters and enol esters.

PubMed

Park, Jihye; Han, Sang Hoon; Sharma, Satyasheel; Han, Sangil; Shin, Youngmi; Mishra, Neeraj Kumar; Kwak, Jong Hwan; Lee, Cheong Hoon; Lee, Jeongmi; Kim, In Su

2014-05-16

A copper-catalyzed oxidative coupling of 2-carbonyl-substituted phenols and 1,3-dicarbonyl compounds with a wide range of dibenzyl or dialkyl ethers is described. This protocol provides an efficient preparation of phenol esters and enol esters in good yields with high chemoselectivity. This method represents an alternative protocol for classical esterification reactions.

Probing occurrence of phenylpropanoids in Morinda citrifolia in relation to foliar diseases.

PubMed

Mandal, Sudhamoy; Rath, Chiranjibi; Gupta, Chandan Kumar; Nath, Vishal; Singh, Hari Shankar

2015-01-01

Accumulation of phenolic compounds in cell walls of different plant organs leading to increased lignification is an early defence response of plants against biotic stress. The aim of this work was to delineate occurrence of cell wall-bound (CWB) phenolic compounds in Morinda citrifolia leaves. Alkaline hydrolysis of the cell wall material of leaf tissues yielded 4-coumaric acid (4-CA) as the major bulk of the phenolic compounds in all Morinda germplasms. Next in line was 4-hydroxybenzoic acid. Other phenolics identified were vanillic acid, 4-hydroxybenzaldehyde, vanillin and ferulic acid. Concentrations of all the CWB phenolics were highest in the germplasm CHN-5, followed by the germplasm CHN-1. Incidentally, these two Morinda germplasms recorded lowest incidence of foliar diseases. Significantly higher amounts of 4-CA in combination with other phenolics may be the reasons for lowest incidence of foliar diseases in CHN-5 and CHN-1 germplasms of M. citrifolia.

Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties.

PubMed

Pinheiro, Patrícia Fontes; Menini, Luciana Alves Parreira; Bernardes, Patrícia Campos; Saraiva, Sérgio Henriques; Carneiro, José Walkimar Mesquita; Costa, Adilson Vidal; Arruda, Társila Rodrigues; Lage, Mateus Ribeiro; Gonçalves, Patrícia Martins; Bernardes, Carolina de Oliveira; Alvarenga, Elson Santiago; Menini, Luciano

2018-01-10

Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1 H NMR, 13 C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 μg mL -1 . Most of the tested compounds presented MIC values ≤220 μg mL -1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.

Simultaneous extraction, identification and quantification of phenolic compounds in Eclipta prostrata using microwave-assisted extraction combined with HPLC-DAD-ESI-MS/MS.

PubMed

Fang, Xinsheng; Wang, Jianhua; Hao, Jifu; Li, Xueke; Guo, Ning

2015-12-01

A simple and rapid method was developed using microwave-assisted extraction (MAE) combined with HPLC-DAD-ESI-MS/MS for the simultaneous extraction, identification, and quantification of phenolic compounds in Eclipta prostrata, a common herb and vegetable in China. The optimized parameters of MAE were: employing 50% ethanol as solvent, microwave power 400 W, temperature 70 °C, ratio of liquid/solid 30 mL/g and extraction time 2 min. Compared to conventional extraction methods, the optimized MAE can avoid the degradation of the phenolic compounds and simultaneously obtained the highest yields of all components faster with less consumption of solvent and energy. Six phenolic acids, six flavonoid glycosides and one coumarin were firstly identified. The phenolic compounds were quantified by HPLC-DAD with good linearity, precision, and accuracy. The extract obtained by MAE showed significant antioxidant activity. The proposed method provides a valuable and green analytical methodology for the investigation of phenolic components in natural plants. Copyright © 2015 Elsevier Ltd. All rights reserved.

The crystallographic, spectroscopic and theoretical studies on (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol molecules

NASA Astrophysics Data System (ADS)

Demirtaş, Güneş; Dege, Necmi; Ağar, Erbil; Uzun, Sümeyye Gümüş

2018-01-01

Two new salicylideneaniline (SA) derivative compounds (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (I), and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (II), have been synthesized and characterized by single crystal X-ray diffraction, IR spectroscopy, 1H NMR, 13C NMR and theoretical methods. Both of the compounds which are Schiff base derivatives are isomer of each other. While the compound (I) crystallizes in centrosymmetric monoclinic space group P 21/c, the compound (II) crystallizes in orthorhombic space group P 212121. The theoretical parameters of the molecules have been calculated by using Hartree-Fock (HF) and density functional theory (DFT/B3LYP) with 6-31G (d,p) basis set. These theoretical parameters have been compared with the experimental parameters obtained by XRD. The experimental geometries of the compounds have been superimposed with the theoretical geometries calculated by HF and DFT methods. Furthermore, the theoretical IR calculations, molecular electrostatic potential maps (MEP) and frontier molecular orbitals have been created for the compounds.

Effects of Virgin Olive Oils Differing in Their Bioactive Compound Contents on Metabolic Syndrome and Endothelial Functional Risk Biomarkers in Healthy Adults: A Randomized Double-Blind Controlled Trial

PubMed Central

Sanchez-Rodriguez, Estefania; Lima-Cabello, Elena; Biel-Glesson, Sara; Fernandez-Navarro, Jose R.; Calleja, Miguel A.; Roca, Maria; Espejo-Calvo, Juan A.; Gil-Extremera, Blas; de la Torre, Rafael; Fito, Montserrat; Covas, Maria-Isabel; Alche, Juan de Dios; Martinez de Victoria, Emilio; Mesa, Maria D.

2018-01-01

The aim of this study was to evaluate the effect of virgin olive oils (VOOs) enriched with phenolic compounds and triterpenes on metabolic syndrome and endothelial function biomarkers in healthy adults. The trial was a three-week randomized, crossover, controlled, double-blind, intervention study involving 58 subjects supplemented with a daily dose (30 mL) of three oils: (1) a VOO (124 ppm of phenolic compounds and 86 ppm of triterpenes); (2) an optimized VOO (OVOO) (490 ppm of phenolic compounds and 86 ppm of triterpenes); and (3) a functional olive oil (FOO) high in phenolic compounds (487 ppm) and enriched with triterpenes (389 ppm). Metabolic syndrome and endothelial function biomarkers were determined in vivo and ex vivo. Plasma high density lipoprotein cholesterol (HDLc) increased after the OVOO intake. Plasma endothelin-1 levels decreased after the intake of the three olive oils, and in blood cell cultures challenged. Daily intake of VOO enriched in phenolic compounds improved plasma HDLc, although no differences were found at the end of the three interventions, while VOO with at least 124 ppm of phenolic compounds, regardless of the triterpenes content improved the systemic endothelin-1 levels in vivo and ex vivo. No effect of triterpenes was observed after three weeks of interventions. Results need to be confirmed in subjects with metabolic syndrome and impaired endothelial function (Clinical Trials number NCT02520739). PMID:29772657

Effects of Virgin Olive Oils Differing in Their Bioactive Compound Contents on Metabolic Syndrome and Endothelial Functional Risk Biomarkers in Healthy Adults: A Randomized Double-Blind Controlled Trial.

PubMed

Sanchez-Rodriguez, Estefania; Lima-Cabello, Elena; Biel-Glesson, Sara; Fernandez-Navarro, Jose R; Calleja, Miguel A; Roca, Maria; Espejo-Calvo, Juan A; Gil-Extremera, Blas; Soria-Florido, Maria; de la Torre, Rafael; Fito, Montserrat; Covas, Maria-Isabel; Alche, Juan de Dios; Martinez de Victoria, Emilio; Gil, Angel; Mesa, Maria D

2018-05-16

The aim of this study was to evaluate the effect of virgin olive oils (VOOs) enriched with phenolic compounds and triterpenes on metabolic syndrome and endothelial function biomarkers in healthy adults. The trial was a three-week randomized, crossover, controlled, double-blind, intervention study involving 58 subjects supplemented with a daily dose (30 mL) of three oils: (1) a VOO (124 ppm of phenolic compounds and 86 ppm of triterpenes); (2) an optimized VOO (OVOO) (490 ppm of phenolic compounds and 86 ppm of triterpenes); and (3) a functional olive oil (FOO) high in phenolic compounds (487 ppm) and enriched with triterpenes (389 ppm). Metabolic syndrome and endothelial function biomarkers were determined in vivo and ex vivo. Plasma high density lipoprotein cholesterol (HDLc) increased after the OVOO intake. Plasma endothelin-1 levels decreased after the intake of the three olive oils, and in blood cell cultures challenged. Daily intake of VOO enriched in phenolic compounds improved plasma HDLc, although no differences were found at the end of the three interventions, while VOO with at least 124 ppm of phenolic compounds, regardless of the triterpenes content improved the systemic endothelin-1 levels in vivo and ex vivo. No effect of triterpenes was observed after three weeks of interventions. Results need to be confirmed in subjects with metabolic syndrome and impaired endothelial function (Clinical Trials number NCT02520739).

Inhibition and kinetic studies of lignin degrading enzymes of Ganoderma boninense by naturally occurring phenolic compounds.

PubMed

Surendran, Arthy; Siddiqui, Yasmeen; Saud, Halimi Mohd; Ali, Nusaibah Syd; Manickam, Sivakumar

2018-05-22

Lignolytic (Lignin degrading) enzyme, from oil palm pathogen Ganoderma boninense Pat. (Syn G. orbiforme (Ryvarden), is involved in the detoxification and the degradation of lignin in the oil palm and is the rate-limiting step in the infection process of this fungus. Active inhibition of lignin degrading enzymes secreted by G. boninense by various naturally occurring phenolic compounds and estimation of efficiency on pathogen suppression was aimed at. In our work, ten naturally occurring phenolic compounds were evaluated for their inhibitory potential towards the lignolytic enzymes of G.boninense. Additionally, the lignin degrading enzymes were characterised. Most of the peholic compounds exhibited an uncompetitive inhibition towards the lignin degrading enzymes. Benzoic acid was the superior inhibitor to the production of lignin degrading enzymes, when compared between the ten phenolic compounds. The inhibitory potential of the phenolic compounds toward the lignin degrading enzymes are higher than that of the conventional metal ion inhibitor. The lignin degrading enzymes were stable in a wide range of pH but were sensitive to higher to temperature. The study demonstrated the inhibitor potential of ten naturally occurring phenolic compounds toward the lignin degrading enzymes of G. boninense with different efficacies. The study has shed a light towards a new management strategy to control BSR in oil palm. It serves as replacement for the existing chemical control. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Degradation of phenolic contaminants in ground water by anaerobic bacteria: St. Louis Park, Minnesota

USGS Publications Warehouse

Ehrlich, G.G.; Goerlitz, D.F.; Godsy, E.M.; Hult, M.F.

1982-01-01

Coal-tar derivatives from a coal-tar distillation and wood-treating plant that operated from 1918 to 1972 at St. Louis Park, Minnesota contaminated the near-surface ground water. Solutions of phenolic compounds and a water-immiscible mixture of polynuclear aromatic compounds accumulated in wetlands near the plant site and entered the aquifer. The concentration of phenolic compounds in the aqueous phase under the wetlands is about 30 mg/1 but decreases to less than 0.2 mg/1 at a distance of 430 m immediately downgradient from the source. Concentrations of naphthalene (the predominant polynuclear compound in the ground water) and sodium (selected as a conservative tracer) range from about 20 mg/1 and 430 mg/1 in the aqueous phase at the source to about 2 mg/1 and 120 mg/1 at 430 m downgradient, respectively. Phenolic compounds and naphthalene are disappearing faster than expected if only dilution were occurring. Sorption of phenolic compounds on aquifer sediments is negligible but naphthalene is slightly sorbed. Anaerobic biodegradation of phenolic compounds is primarily responsible for the observed attenuation. Methane was found only in water samples from the contaminated zone (2-20 mg/1). Methane-producing bacteria were found only in water from the contaminated zone. Methane was produced in laboratory cultures of contaminated water inoculated with bacteria from the contaminated zone. Evidence for anaerobic biodegradation of naphthalene under either field or laboratory conditions was not obtained.

Simple quantification of phenolic compounds present in the minor fraction of virgin olive oil by LC-DAD-FLD.

PubMed

Godoy-Caballero, M P; Acedo-Valenzuela, M I; Galeano-Díaz, T

2012-11-15

This paper presents the results of the study on the extraction, identification and quantification of a group of important phenolic compounds in virgin olive oil (VOO) samples, obtained from olives of various varieties, by liquid chromatography coupled to UV-vis and fluorescence detection. Sixteen phenolic compounds belonging to different families have been identified and quantified spending a total time of 25 min. The linearity was examined by establishing the external standard calibration curves. Four order linear ranges and limits of detection ranging from 0.02 to 0.6 μg mL(-1) and 0.006 to 0.3 μg mL(-1) were achieved using UV-vis and fluorescence detection, respectively. Regarding the real samples, for the determination of the phenolic compounds in higher concentrations (hydroxytyrosol and tyrosol) a simple liquid-liquid extraction with ethanol was used to make the sample compatible with the mobile phase. Recovery values close to 100% were obtained. However, a previous solid phase extraction with Diol cartridges was necessary to concentrate and separate the minor phenolic compounds of the main interferences. The parameters affecting this step were carefully optimized and, after that, recoveries near 80-100% were obtained for the rest of the studied phenolic compounds. Also, the limits of detection were improved 15 times. Finally, the standard addition method was carried out for each of the analytes and no matrix effect was found, so the quantification of the 16 phenolic compounds from different monovarietal VOO was carried out by using the corresponding external standard calibration plot. Copyright © 2012 Elsevier B.V. All rights reserved.

Alkoxyl- and carbon-centered radicals as primary agents for degrading non-phenolic lignin-substructure model compounds.

PubMed

Ohashi, Yasunori; Uno, Yukiko; Amirta, Rudianto; Watanabe, Takahito; Honda, Yoichi; Watanabe, Takashi

2011-04-07

Lignin degradation by white-rot fungi proceeds via free radical reaction catalyzed by oxidative enzymes and metabolites. Basidiomycetes called selective white-rot fungi degrade both phenolic and non-phenolic lignin substructures without penetration of extracellular enzymes into the cell wall. Extracellular lipid peroxidation has been proposed as a possible ligninolytic mechanism, and radical species degrading the recalcitrant non-phenolic lignin substructures have been discussed. Reactions between the non-phenolic lignin model compounds and radicals produced from azo compounds in air have previously been analysed, and peroxyl radical (PR) is postulated to be responsible for lignin degradation (Kapich et al., FEBS Lett., 1999, 461, 115-119). However, because the thermolysis of azo compounds in air generates both a carbon-centred radical (CR) and a peroxyl radical (PR), we re-examined the reactivity of the three radicals alkoxyl radical (AR), CR and PR towards non-phenolic monomeric and dimeric lignin model compounds. The dimeric lignin model compound is degraded by CR produced by reaction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH), which under N(2) atmosphere cleaves the α-β bond in 1-(4-ethoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol to yield 4-ethoxy-3-methoxybenzaldehyde. However, it is not degraded by the PR produced by reaction of Ce(4+)/tert-BuOOH. In addition, it is degraded by AR produced by reaction of Ti(3+)/tert-BuOOH. PR and AR are generated in the presence and absence of veratryl alcohol, respectively. Rapid-flow ESR analysis of the radical species demonstrates that AR but not PR reacts with the lignin model compound. Thus, AR and CR are primary agents for the degradation of non-phenolic lignin substructures.

Phenolic compounds are highly correlated to the antioxidant capacity of genotypes of Oenocarpus distichus Mart. fruits.

PubMed

Brabo de Sousa, Sérgio Henrique; de Andrade Mattietto, Rafaella; Campos Chisté, Renan; Carvalho, Ana Vânia

2018-06-01

This research aimed to evaluate 32 genotypes of Oenocarpus distichus fruits regarding the contents of total phenolic compounds, flavonoids, flavanols, monomeric anthocyanins, antioxidant capacity (ABTS and DPPH assays), and the phenolic compound profiles of the five genotypes that presented the highest yields of bioactive compounds. The genotypes were harvested in three different locations in Pará State, Northern Brazil, (Belém, São João do Araguaia and Marabá). Among the 32 genotypes, the highest bioactive compound contents and antioxidant capacity were found for three genotypes harvested in Belém (B-3, B-7 and B-8) and two harvested in São João do Araguaia (SJ-1 and SJ-4), and the total phenolic compounds varied from 131.97 to 363.01 mg gallic acid equivalent/100 g, total flavonoids from 24.23 to 38.19 mg quercetin equivalent/100 g, total flavanols from 72.29 to 259.18 mg catechin equivalent/100 g, and monomeric anthocyanins from 21.31 to 67.76 mg cyanidin 3-rutinoside/100 g. The main phenolic compounds tentatively identified in the five selected genotypes were cyanidin 3-O-rutinoside (48.47 to 196.51 μg/g), which could be identified and quantified as the major phenolic compound in Oenocarpus distichus fruits, for the first time, followed by chlorogenic acid (0.71 to 64.56 μg/g) and rutin (13.98 to 56.76 μg/g). Copyright © 2018 Elsevier Ltd. All rights reserved.

Inhibitory effects of benzimidazole containing new phenolic Mannich bases on human carbonic anhydrase isoforms hCA I and II.

PubMed

Gul, Halise Inci; Yazici, Zehra; Tanc, Muhammet; Supuran, Claudiu T

2016-12-01

New phenolic mono and bis Mannich bases incorporating benzimidazole, such as 2-(aminomethyl)-4-(1H-benzimidazol-2-yl)phenol and 2,6-bis(aminomethyl)-4-(1H-benzimidazol-2-yl)phenol were synthesized starting from 4-(1H-benzimidazol-2-yl)phenol. Amines used for the synthesis included dimethylamine, pyrrolidine, piperidine, N-methylpiperazine and morpholine. The CA inhibitory properties of these compounds were tested on the human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and hCA II. These new compounds, as many phenols show moderate CA inhibitory properties.

Stability of lipid encapsulated phenolic acid particles

USDA-ARS?s Scientific Manuscript database

Phenolic compounds such as ferulic acid and p-coumaric acids are potential bioactive additives for use in animal feeds to replace current antioxidants and antimicrobial compounds. These compounds are ubiquitous in plants and may be obtained from commodity grain crops and waste biomass. Encapsulation...

Anticarcinogenic Effect of Spices Due to Phenolic and Flavonoid Compounds-In Vitro Evaluation on Prostate Cells.

PubMed

Lackova, Zuzana; Buchtelova, Hana; Buchtova, Zaneta; Klejdus, Borivoj; Heger, Zbynek; Brtnicky, Martin; Kynicky, Jindrich; Zitka, Ondrej; Adam, Vojtech

2017-09-28

This study shows the effects of spices, and their phenolic and flavonoid compounds, on prostate cell lines (PNT1A, 22RV1 and PC3). The results of an MTT assay on extracts from eight spices revealed the strongest inhibitory effects were from black pepper and caraway seed extracts. The strongest inhibitory effect on prostatic cells was observed after the application of extracts of spices in concentration of 12.5 mg·mL -1 . An LC/MS analysis identified that the most abundant phenolic and flavonoid compounds in black pepper are 3,4-dihydroxybenzaldehyde and naringenin chalcone, while the most abundant phenolic and flavonoid compounds in caraway seeds are neochlorogenic acid and apigenin. Using an MTT assay for the phenolic and flavonoid compounds from spices, we identified the IC 50 value of ~1 mmol·L -1 PNT1A. The scratch test demonstrated that the most potent inhibitory effect on PNT1A, 22RV1 and PC3 cells is from the naringenin chalcone contained in black pepper. From the spectrum of compounds assessed, the naringenin chalcone contained in black pepper was identified as the most potent inhibitor of the growth of prostate cells.

Importance of phenols structure on their activity as antinitrosating agents: A kinetic study

PubMed Central

Pessêgo, Márcia; Rosa da Costa, Ana M; Moreira, José A.

2011-01-01

Objective: Nitrosative deamination of DNA bases induced by reaction with reactive nitrogen species (RNS) has been pointed out as a probable cause of mutagenesis. (Poly)phenols, present in many food items from the Mediterranean diet, are believed to possess antinitrosating properties due to their RNS scavenging ability, which seems to be related to their structure. It has been suggested that phenolic compounds will react with the above-mentioned species more rapidly than most amino compounds, thus preventing direct nitrosation of the DNA bases and their transnitrosation from endogenous N-nitroso compounds, or most likely from the transient N-nitrosocompounds formed in vivo. Materials and Methods: In order to prove that assumption, a kinetic study of the nitroso group transfer from a N-methyl-N-nitrosobenzenesulfonamide (N-methyl-N-nitroso-4-methylbenzenesulfonamide, MeNMBS) to the DNA bases bearing an amine group and to a series of phenols was carried out. In the transnitrosation of phenols, the formation of nitrosophenol was monitored by Ultraviolet (UV) / Visible spectroscopy, and in the reactions of the DNA bases, the consumption of MeNMBS was followed by high performance liquid chromatography (HPLC). Results: The results obtained point to the transnitrosation of DNA bases being negligible, as well as that of phenols bearing electron-withdrawing groups. Phenols with methoxy substituents in positions 2, 4, and / or 6, although they seemed to react, did not afford the expected product. Phenols with electron-releasing substituents, unless these blocked the oxygen atom, reacted with our model compound at an appreciable rate. O-nitrosation of the phenolate ion followed by rearrangement of the C-nitrosophenol seemed to be involved. Conclusion: This study provided evidence that the above compounds might actually act as antinitrosating agents in vivo. PMID:21430963

Ultra-high performance supercritical fluid chromatography of lignin-derived phenols from alkaline cupric oxide oxidation.

PubMed

Sun, Mingzhe; Lidén, Gunnar; Sandahl, Margareta; Turner, Charlotta

2016-08-01

Traditional chromatographic methods for the analysis of lignin-derived phenolic compounds in environmental samples are generally time consuming. In this work, an ultra-high performance supercritical fluid chromatography method with a diode array detector for the analysis of major lignin-derived phenolic compounds produced by alkaline cupric oxide oxidation was developed. In an analysis of a collection of 11 representative monomeric lignin phenolic compounds, all compounds were clearly separated within 6 min with excellent peak shapes, with a limit of detection of 0.5-2.5 μM, a limit of quantification of 2.5-5.0 μM, and a dynamic range of 5.0-2.0 mM (R(2) > 0.997). The new ultra-high performance supercritical fluid chromatography method was also applied for the qualitative and quantitative analysis of lignin-derived phenolic compounds obtained upon alkaline cupric oxide oxidation of a commercial humic acid. Ten out of the previous eleven model compounds could be quantified in the oxidized humic acid sample. The high separation power and short analysis time obtained demonstrate for the first time that supercritical fluid chromatography is a fast and reliable technique for the analysis of lignin-derived phenols in complex environmental samples. © 2016 The Authors, Journal of Separation Science Published by WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Tapping the Bioactivity Potential of Residual Stream from Its Pretreatments May Be a Green Strategy for Low-Cost Bioconversion of Rice Straw.

PubMed

Chen, Xingxuan; Wang, Xiahui; Xue, Yiyun; Zhang, Tian-Ao; Hu, Jiajun; Tsang, Yiu Fai; Gao, Min-Tian

2018-04-16

In this study, it was found that the residual stream from pretreatments of rice straw exhibited high antioxidant activity. Assays based on the Folin-Ciocalteu colorimetric method confirmed that the residual stream contained large amounts of phenolic compounds. Three antioxidant assays were employed to evaluate the bioactivity of the residual stream. Strong linear correlations existed among the release of phenolic compounds, saccharification efficiency, and antioxidant activity. The alkaline pretreatment provided a much greater release of phenolic compounds, especially phenolic acids, compared to the acid pretreatment, and consequently, it had stronger linear correlations than the acid pretreatment. Antibacterial experiments demonstrated the ability of the phenolic compounds in the residual stream to inhibit the growth of microorganisms, indicating the potential of these compounds as antimicrobial agents. To discuss the possibility of the co-production of antimicrobial agents and biofuels/biochemicals, both acid and alkaline pretreatments were optimized using response surface methodology. Under the optimal conditions, 285.7 g glucose could be produced from 1 kg rice straw with the co-production of 3.84 g FA and 6.98 g p-CA after alkaline pretreatment. These results show that the recovery of phenolic compounds from the residual stream could be a green strategy for the low-cost bioconversion of rice straw.

Effects of furan derivatives and phenolic compounds on electricity generation in microbial fuel cells

NASA Astrophysics Data System (ADS)

Catal, Tunc; Fan, Yanzhen; Li, Kaichang; Bermek, Hakan; Liu, Hong

Lignocellulosic biomass is an attractive fuel source for MFCs due to its renewable nature and ready availability. Furan derivatives and phenolic compounds could be potentially formed during the pre-treatment process of lignocellulosic biomass. In this study, voltage generation from these compounds and the effects of these compounds on voltage generation from glucose in air-cathode microbial fuel cells (MFCs) were examined. Except for 5-hydroxymethyl furfural (5-HMF), all the other compounds tested were unable to be utilized directly for electricity production in MFCs in the absence of other electron donors. One furan derivate, 5-HMF and two phenolic compounds, trans-cinnamic acid and 3,5-dimethoxy-4-hydroxy-cinnamic acid did not affect electricity generation from glucose at a concentration up to 10 mM. Four phenolic compounds, including syringaldeyhde, vanillin, trans-4-hydroxy-3-methoxy, and 4-hydroxy cinnamic acids inhibited electricity generation at concentrations above 5 mM. Other compounds, including 2-furaldehyde, benzyl alcohol and acetophenone, inhibited the electricity generation even at concentrations less than 0.2 mM. This study suggests that effective electricity generation from the hydrolysates of lignocellulosic biomass in MFCs may require the employment of the hydrolysis methods with low furan derivatives and phenolic compounds production, or the removal of some strong inhibitors prior to the MFC operation, or the improvement of bacterial tolerance against these compounds through the enrichment of new bacterial cultures or genetic modification of the bacterial strains.

Rapid determination of phenolic compounds and alkaloids of carob flour by improved liquid chromatography tandem mass spectrometry.

PubMed

Ortega, Nàdia; Macià, Alba; Romero, Maria-Paz; Trullols, Esther; Morello, Jose-Ramón; Anglès, Neus; Motilva, Maria-Jose

2009-08-26

An improved chromatographic method was developed using ultra-performance liquid chromatography-tandem mass spectrometry to identify and quantify phenolic compounds and alkaloids, theobromine and caffeine, in carob flour samples. The developed method has been validated in terms of speed, sensitivity, selectivity, peak efficiency, linearity, reproducibility, limits of detection, and limits of quantification. The chromatographic method allows the identification and quantification of 20 phenolic compounds, that is, phenolic acids, flavonoids, and their aglycone and glucoside forms, together with the determination of the alkaloids, caffeine and theobromine, at low concentration levels all in a short analysis time of less than 20 min.

Xylosylation of Phenolic Hydroxyl Groups of the Monomeric Lignin Model Compounds 4-Methylguaiacol and Vanillyl Alcohol by Coriolus versicolor

PubMed Central

Kondo, Ryuichiro; Yamagami, Hikari; Sakai, Kokki

1993-01-01

When 4-methylguaiacol (MeG), a phenolic lignin model compound, was added to a culture that was inoculated with Coriolus versicolor, it was bioconverted into 2-methoxy-4-methylphenyl β-d-xyloside (MeG-Xyl). The phenolic hydroxyl group of vanillyl alcohol was much more extensively xylosylated than the alcoholic hydroxyl group. When a mixture of MeG and commercial UDP-xylose was incubated with cell extracts of mycelia, transformation of UDP-xylose into MeG-Xyl was observed. This result suggested that UDP-xylosyltransferase was involved in the xylosylation of phenolic hydroxyl groups of lignin model compounds. PMID:16348869

UHPLC-MS/MS phenolic profiling and in vitro antioxidant activities of Inula graveolens (L.) Desf.

PubMed

Silinsin, Muzaffer; Bursal, Ercan

2018-06-01

Inula graveolens (L.) Desf. is an annual aromatic herb which has various uses on alternative medicine in many region of the world. In this study, antioxidant activities of ethanol and water extracts of the plant leaves were determined by in vitro DPPH method and phenolic composition of the plant sample was determined by LC-MS/MS analysis. The results showed that chlorogenic acid, quinic acid, hyperoside, protocatechuic acid and quercetin were the major phenolic compounds among the 27 standard compounds. The significant antioxidant capacity of the plant might be related with the high abundance of phenolic compounds.

Monte Carlo simulation of energy absorbed in phenolic ESR dosimeters added with gadolinium exposed to thermal, epithermal and fast neutrons

NASA Astrophysics Data System (ADS)

Longo, A.; Collura, G.; Gallo, S.; Bartolotta, A.; Marrale, M.

2017-11-01

In this work analyses of the energy released per unit mass in phenolic compound exposed to neutron beams were performed with the aim of predicting the increase in dose achievable by addition of gadolinium (Gd) inside the pellets. In particular, Monte Carlo (MC) simulations were carried out for IRGANOX® 1076 phenolic compound irradiated with neutron beams with different energy spectra at various depths inside a water phantom. The addition of gadolinium increases sensitivity of phenolic ESR (electron spin resonance) dosimeters to neutrons thanks to the high gadolinium cross section for neutron capture and to the large number of secondary particles (mainly Auger and internal conversion electrons) which are able to release energy inside the sensitive material layers. For small depths in water phantom and low energy neutron spectra the increase in dose due to gadolinium is large (more than a factor 50). The enhancement is smaller in case of epithermal neutron beam, whereas the increase in dose for fast neutrons is less than 50%. In order to have a comparison with other ESR dosimeters the energy released per unit mass in phenolic compound was compared with that calculated in alanine pellets. For thermal neutron beams the energy released in phenolic compound with gadolinium is comparable to that released in alanine for small depths in phantom, whereas it is larger than in alanine for large depths. In case of epithermal and fast neutron beams the energy released in phenolic compound is larger than in alanine samples because the elastic scattering with hydrogen nuclei is more probable for high neutron energies and this phenolic compound is characterized by an higher number of 1H nuclei than alanine. All results here found suggest that these phenolic pellets could be fruitfully used for dosimetric applications in Neutron Capture Therapy.

Use of image analysis to estimate anthocyanin and UV-excited fluorescent phenolic compound levels in strawberry fruit

PubMed Central

Yoshioka, Yosuke; Nakayama, Masayoshi; Noguchi, Yuji; Horie, Hideki

2013-01-01

Strawberry is rich in anthocyanins, which are responsible for the red color, and contains several colorless phenolic compounds. Among the colorless phenolic compounds, some, such as hydroxycinammic acid derivatives, emit blue-green fluorescence when excited with ultraviolet (UV) light. Here, we investigated the effectiveness of image analyses for estimating the levels of anthocyanins and UV-excited fluorescent phenolic compounds in fruit. The fruit skin and cut surface of 12 cultivars were photographed under visible and UV light conditions; colors were evaluated based on the color components of images. The levels of anthocyanins and UV-excited fluorescent compounds in each fruit were also evaluated by spectrophotometric and high performance liquid chromatography (HPLC) analyses, respectively and relationships between these levels and the image data were investigated. Red depth of the fruits differed greatly among the cultivars and anthocyanin content was well estimated based on the color values of the cut surface images. Strong UV-excited fluorescence was observed on the cut surfaces of several cultivars, and the grayscale values of the UV-excited fluorescence images were markedly correlated with the levels of those fluorescent compounds as evaluated by HPLC analysis. These results indicate that image analyses can select promising genotypes rich in anthocyanins and fluorescent phenolic compounds. PMID:23853516

Ultrasound-assisted extraction of phenolic compounds from Cratoxylum formosum ssp. formosum leaves using central composite design and evaluation of its protective ability against H2O2-induced cell death.

PubMed

Yingngam, Bancha; Monschein, Marlene; Brantner, Adelheid

2014-09-01

To optimize the processing parameters for phenolic compounds extracted from Cratoxylum formosum ssp. formosum leaves using an ultrasound-assisted extraction and to evaluate its protective ability against H2O2-induced cell death. The influence of three independent variables including ethanol concentration (%), extraction temperature (°C) and extraction time (min) on the extraction yield of phenolic compounds were optimized using a central composite design-based response surface methodology. The obtained extract was assessed for its antioxidant activity by DPPH(•) and ABTS(•)(+) methods. Cellular protective ability against H2O2-induced cell death was evaluated on HEK293 cells using the MTT assay. The optimal conditions to achieve maximal yields of phenolic compounds were ethanol concentration of 50.33% (v/v), temperature of 65 °C, and extractiontion time of 15 min. The yield of phenolic compounds was (40.00±1.00) mg gallic acid equivalent/g dry powder which matched well with the values predicted from the proposed model. These conditions resulted in a higher efficiency concerning the extraction of phenolics compared to a conventional heat reflux extraction by providing shorter extraction time and reduced energy consumption. 5-O-caffeoylquinic acid identified by high performance liquid chromatography-diode array detector-electron spin ionization-mass spectrometry was the major compound in the obtained extract [(41.66±0.07) mg/g plant extract]. The obtained extract showed a strong ability to scavenge both DPPH(•) and ABTS(•)(+) free radicals and exhibited additionally good ability to protect HEK293 cells death against oxidative stress. These results indicate the suitability of ultrasound-assisted extraction for the extraction of phenolic compounds from Cratoxylum formosum ssp. formosum leaves. This phenolic-enriched extract can be used as valuable antioxidant source for health benefits. Copyright © 2014 Hainan Medical College. Published by Elsevier B.V. All rights reserved.

Comprehensive characterization of phenolic and other polar compounds in the seed and seed coat of avocado by HPLC-DAD-ESI-QTOF-MS.

PubMed

Figueroa, Jorge G; Borrás-Linares, Isabel; Lozano-Sánchez, Jesús; Segura-Carretero, Antonio

2018-03-01

Avocado seed and seed coat are important by-products from avocado industrialization, with important functional properties. The aim of the present study was to determine the phenolic profile and other polar compounds of avocado seed and seed coat using accelerated solvent extraction (ASE) and liquid chromatography coupled to Ultra-High-Definition Accurate-Mass Q-TOF. In this research 84 compounds were identified, within eight subclass group, among these 45 phenolic compounds were identified for first time in avocado seed. Condensed tannins, phenolic acids and flavonoids were the most representative groups in both samples. As far as we are concerned, this is the first time that avocado seed coat has been studied regarding its phenolic compounds using such a powerful instrumental technique. In addition, the radical-scavenging activities were analysed in order to estimate the antioxidant potential of extracts. These results point out that avocado seed and seed coat constitute a source of bioactive ingredients for its use in the food, cosmetic or pharmaceutical sector. Copyright © 2017 Elsevier Ltd. All rights reserved.

Nanoliposomal carriers for improvement the bioavailability of high - valued phenolic compounds of pistachio green hull extract.

PubMed

Rafiee, Zahra; Barzegar, Mohsen; Sahari, Mohammad Ali; Maherani, Behnoush

2017-04-01

In present study, nanoliposomes were prepared by thin hydration method with different concentrations of phenolic compounds (500, 750 and 1000ppm) of pure extract and lecithin (1, 2 and 3%w/w) and characterized by considering the particle size, polydispersity index (PDI), zeta potential, encapsulation efficiency (EE) and morphology. The results showed that nanoliposome (90.39-103.78nm) had negative surface charge varied from -51.5±0.9 to -40.2±0.2mV with a narrow size distribution (PDI≈0.069-0.123). Nanoliposomes composed of 1% lecithin with 1000ppm of phenolic compounds had the highest EE (52.93%). The FTIR analysis indicated the formation of hydrogen bonds between the polar zone of phospholipid and the OH groups of phenolic compounds. Phenolic compounds also increased phase transition temperature (Tc) of nanoliposomes (2.01-7.24°C). Moreover, nanoliposomes had considerable stability during storage. Consequently, liposome is an efficient carrier for protection and improving PGHE biofunctional actives in foodstuffs. Copyright © 2016 Elsevier Ltd. All rights reserved.

Exploring reserve lots of Cymbopogon citratus, Aloysia citrodora and Thymus × citriodorus as improved sources of phenolic compounds.

PubMed

Rita, Ingride; Pereira, Carla; Barros, Lillian; Ferreira, Isabel C F R

2018-08-15

Given the increasing consumers demand for novelty, tea companies have been presenting new added value products such as reserve lots of aromatic plants. Herein, infusions from different lots of three aromatic plants were assessed in terms of phenolic composition (HPLC-DAD-ESI/MS) and antioxidant properties (reducing power, free radical scavenging and lipid peroxidation inhibition capacity). Cymbopogon citratus (C. citratus; main compound 5-O-caffeoylquinic acid) and Aloysia citrodora (A. citrodora; prevalence of verbascoside) reserve lots revealed higher phenolic compounds concentration than the respective standard lots. Thymus × citriodorus (T. citriodorus; main compound rosmarinic acid) standard lot presented higher amounts of phenolic acids than the reserve lot, nonetheless, total flavonoids and phenolic compounds were not significantly different. The differences between both lots antioxidant activity were more noticeable in C. citratus, with the reserve lot presenting the highest activity. This study provides evidence of the differences between these plants chemical composition and bioactivity depending on the harvesting conditions. Copyright © 2018 Elsevier Ltd. All rights reserved.

Antioxidant activity and phenolic compounds in organic red wine using different winemaking techniques.

PubMed

Mulero, Juana; Zafrilla, Pilar; Cayuela, Jose M; Martínez-Cachá, Adela; Pardo, Francisco

2011-04-01

Wine phenolic composition depends on the grapes used to make wine and on vinification conditions. The occurrence of these biological compounds has stimulated numerous studies focused on understanding the mechanisms that influence their concentrations in wine. This article studied the effect of different vinification techniques on the antioxidant activity and on the phenolic compounds of red wine made from the variety of Monastrell grapes obtained by organic culture. To this purpose, 3 different vinification procedures were carried out: vinification after prolonged maceration, vinification with the addition of enological enzymes, and traditional vinification procedures (used as control).The results showed similar values of antioxidant activity in all 3 types of wine elaborated and found no differences in the concentrations of the different types of phenolic compounds in wine made with the 3 different methods. The evolution of antioxidant activity and phenolic compounds tested in wines during 3 mo of storage showed a similar pattern. Organic wine has acquired an important role in the economic world and its important, working in oenology to research in this field.

Optimization of the ultrasound-assisted extraction of anthocyanins and total phenolic compounds in mulberry (Morus nigra) pulp.

PubMed

Espada-Bellido, Estrella; Ferreiro-González, Marta; Carrera, Ceferino; Palma, Miguel; Barroso, Carmelo G; Barbero, Gerardo F

2017-03-15

New ultrasound-assisted extraction methods for the determination of anthocyanins and total phenolic compounds present in mulberries have been developed. Several extraction variables, including methanol composition (50-100%), temperature (10-70°C), ultrasound amplitude (30-70%), cycle (0.2-0.7s), solvent pH (3-7) and solvent-solid ratio (10:1.5-20:1.5) were optimized. A Box-Behnken design in conjunction with a response surface methodology was employed to optimize the conditions for the maximum response based on 54 different experiments. Two response variables were considered: total anthocyanins and total phenolic compounds. Extraction temperature and solvent composition were found to be the most influential parameters for anthocyanins (48°C and 76%) and phenolic compounds (64°C and 61%). The developed methods showed high reproducibility and repeatability (RSD<5%). Finally, the new methods were successfully applied to real samples in order to investigate the presence of anthocyanins and total phenolic compounds in several mulberry jams. Copyright © 2016 Elsevier Ltd. All rights reserved.

Lignin-derived oak phenolics: a theoretical examination of additional potential health benefits of red wine.

PubMed

Setzer, William N

2011-08-01

Lignin-derived phenolic compounds can be extracted from oak barrels during the aging of red wine, and it is hypothesized that these compounds may contribute to the health benefits of red wine by their antioxidant, radical-scavenging, or chemopreventive activities. Density functional calculations (B3LYP/6-311++G) support the radical-scavenging abilities of the oak phenolics. Sinapaldehyde, syringaldehyde, syringol, and syringylacetone all have bond dissociation energies that are lower than resveratrol and comparable to the flavonoid catechin. Molecular docking studies of the oak phenolics with known resveratrol protein targets also show that these compounds dock favorably to the protein targets. Thus, lignin-derived oak phenolics, although found in small concentrations, may contribute to the beneficial antioxidant, chemopreventive, and cardioprotective effects of red wine.

Wine phenolic compounds influence the production of volatile phenols by wine-related lactic acid bacteria.

PubMed

Silva, I; Campos, F M; Hogg, T; Couto, J A

2011-08-01

To evaluate the effect of wine phenolic compounds on the production of volatile phenols (4-vinylphenol [4VP] and 4-ethylphenol [4EP]) from the metabolism of p-coumaric acid by lactic acid bacteria (LAB). Lactobacillus plantarum, Lactobacillus collinoides and Pediococcus pentosaceus were grown in MRS medium supplemented with p-coumaric acid, in the presence of different phenolic compounds: nonflavonoids (hydroxycinnamic and benzoic acids) and flavonoids (flavonols and flavanols). The inducibility of the enzymes involved in the p-coumaric acid metabolism was studied in resting cells. The hydroxycinnamic acids tested stimulated the capacity of LAB to synthesize volatile phenols. Growth in the presence of hydroxycinnamic acids, especially caffeic acid, induced the production of 4VP by resting cells. The hydroxybenzoic acids did not significantly affect the behaviour of the studied strains. Some of the flavonoids showed an effect on the production of volatile phenols, although strongly dependent on the bacterial species. Relatively high concentrations (1 g l(-1) ) of tannins inhibited the synthesis of 4VP by Lact. plantarum. Hydroxycinnamic acids were the main compounds stimulating the production of volatile phenols by LAB. The results suggest that caffeic and ferulic acids induce the synthesis of the cinnamate decarboxylase involved in the metabolism of p-coumaric acid. On the other hand, tannins exert an inhibitory effect. This study highlights the capacity of LAB to produce volatile phenols and that this activity is markedly influenced by the phenolic composition of the medium. © 2011 The Authors. Journal of Applied Microbiology © 2011 The Society for Applied Microbiology.

Spectrophotometric Determination of Phenolic Antioxidants in the Presence of Thiols and Proteins

PubMed Central

Avan, Aslı Neslihan; Demirci Çekiç, Sema; Uzunboy, Seda; Apak, Reşat

2016-01-01

Development of easy, practical, and low-cost spectrophotometric methods is required for the selective determination of phenolic antioxidants in the presence of other similar substances. As electron transfer (ET)-based total antioxidant capacity (TAC) assays generally measure the reducing ability of antioxidant compounds, thiols and phenols cannot be differentiated since they are both responsive to the probe reagent. In this study, three of the most common TAC determination methods, namely cupric ion reducing antioxidant capacity (CUPRAC), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt/trolox equivalent antioxidant capacity (ABTS/TEAC), and ferric reducing antioxidant power (FRAP), were tested for the assay of phenolics in the presence of selected thiol and protein compounds. Although the FRAP method is almost non-responsive to thiol compounds individually, surprising overoxidations with large positive deviations from additivity were observed when using this method for (phenols + thiols) mixtures. Among the tested TAC methods, CUPRAC gave the most additive results for all studied (phenol + thiol) and (phenol + protein) mixtures with minimal relative error. As ABTS/TEAC and FRAP methods gave small and large deviations, respectively, from additivity of absorbances arising from these components in mixtures, mercury(II) compounds were added to stabilize the thiol components in the form of Hg(II)-thiol complexes so as to enable selective spectrophotometric determination of phenolic components. This error compensation was most efficient for the FRAP method in testing (thiols + phenols) mixtures. PMID:27529232

A review of molecular mechanisms of the anti-leukemic effects of phenolic compounds in honey.

PubMed

Abubakar, Murtala B; Abdullah, Wan Zaidah; Sulaiman, Siti Amrah; Suen, Ang Boon

2012-11-15

Hematologic malignancies constitute about 9% of all new cases of cancers as reported via the GLOBOCAN series by International Agency for Research on Cancer (IARC) in 2008. So far, the conventional therapeutic and surgical approaches to cancer therapy have not been able to curtail the rising incidence of cancers, including hematological malignancies, worldwide. The last decade has witnessed great research interest in biological activities of phenolic compounds that include anticancer, anti-oxidation and anti-inflammation, among other things. A large number of anticancer agents combat cancer through cell cycle arrest, induction of apoptosis and differentiation, as well as through inhibition of cell growth and proliferation, or a combination of two or more of these mechanisms. Various phenolic compounds from different sources have been reported to be promising anticancer agents by acting through one of these mechanisms. Honey, which has a long history of human consumption both for medicinal and nutritional uses, contains a variety of phenolic compounds such as flavonoids, phenolic acids, coumarins and tannins. This paper presents a review on the molecular mechanisms of the anti-leukemic activity of various phenolic compounds on cell cycle, cell growth and proliferation and apoptosis, and it advocates that more studies should be conducted to determine the potential role of honey in both chemoprevention and chemotherapy in leukemia.

Chemical composition and antioxidant activity of phenolic compounds from Dioscorea (Yam) leaves.

PubMed

Zhou, Li; Shi, Xinmin; Ren, Xiangmei; Qin, Zhihong

2018-05-01

This study was aimed to assess the potential of Dioscorea (yam) leaves as a source of antioxidants. Microwave-assisted extraction (MAE) process was used to prepare the extracts. The phenolic compounds in Dioscorea leaves extracts were analyzed by HPLC-DAD-ESI-MS/MS method and the contents of major compounds were determined. Results indicated that a total of 17 phenolic compounds were separated identified by means of UV and mass spectra compared with authentic reference substances and/or reported values in the literature. The main phenolic compound was rosmarinic acid and its highest amount was found in Dioscorea glabra Roxb. leaves (22.31±1.33 mg/g DW). Rutin was the dominant flavonoid followed by quercetin which highest amount was found in Dioscorea alata leaves (8.66±0.29 mg/g DW). Antioxidant activity of the extracts was estimated by the use of DPPH and ABTS assays. Both kinds of leaves exhibited satisfied antioxidant capacity which was correlated with phenolic contents. In the cytoprotective effect on HUVECs viability assay, Dioscorea glabra Roxb. leaves extract was found to be more active than that of Dioscorea alata against H 2 O 2 -induced oxidative stress. Our findings support the promising role of Dioscorea leaves that can be used as an interesting source of phenolic antioxidants.

Reduction of soluble nitrogen and mobilization of plant nutrients in soils from U.S. northern Great Plains agroecosystems by phenolic compounds

USDA-ARS?s Scientific Manuscript database

Phenolic plant secondary metabolites actively participate in a broad range of important reactions that affect livestock, plants and soil. In soil, phenolic compounds can affect nutrient dynamics and mobility of metals but their role in northern Great Plains agroecosystems is largely unknown. We eval...

Phenolic profiles and polyphenol oxidase (PPO) gene expression of red clover (Trifolium pratense) selected for decreased postharvest browning

USDA-ARS?s Scientific Manuscript database

Red clover (Trifolium pratense L.) is a legume forage abundant in phenolic compounds. It tends to brown when cut for hay, due to oxidation of phenolic compounds catalyzed by polyphenol oxidase (PPO), and subsequent binding to proteins. Selecting for a greener hay may provide information about the re...

Phenolic content, anthocyanins and antiradical capacity of diverse purple bran rice genotypes as compared to other bran colors

USDA-ARS?s Scientific Manuscript database

Phenolic compounds reportedly may reduce the risk of developing chronic disease and their risk factors. Anthocyanins are flavonoids, a subgroup of phenolic compounds in purple colored whole grain rice that have shown these health benefits in animal studies and human clinical trials. We studied the g...

Analysis of Phenolic Compounds and Antioxidant Activity in Wild Blackberry Fruits

PubMed Central

Oszmiański, Jan; Nowicka, Paulina; Teleszko, Mirosława; Wojdyło, Aneta; Cebulak, Tomasz; Oklejewicz, Krzysztof

2015-01-01

Twenty three different wild blackberry fruit samples were assessed regarding their phenolic profiles and contents (by LC/MS quadrupole time-of-flight (QTOF) and antioxidant activity (ferric reducing ability of plasma (FRAP) and 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS)) by two different extraction methods. Thirty four phenolic compounds were detected (8 anthocyanins, 15 flavonols, 3 hydroxycinnamic acids, 6 ellagic acid derivatives and 2 flavones). In samples, where pressurized liquid extraction (PLE) was used for extraction, a greater increase in yields of phenolic compounds was observed, especially in ellagic acid derivatives (max. 59%), flavonols (max. 44%) and anthocyanins (max. 29%), than after extraction by the ultrasonic technique extraction (UAE) method. The content of phenolic compounds was significantly correlated with the antioxidant activity of the analyzed samples. Principal component analysis (PCA) revealed that the PLE method was more suitable for the quantitative extraction of flavonols, while the UAE method was for hydroxycinnamic acids. PMID:26132562

Comparison of content in phenolic compounds, polyphenol oxidase, and peroxidase in grains of fifty sorghum varieties from burkina faso.

PubMed

Dicko, Mamoudou H; Hilhorst, Riet; Gruppen, Harry; Traore, Alfred S; Laane, Colja; van Berkel, Willem J H; Voragen, Alphons G J

2002-06-19

Analysis of fifty sorghum [Sorghum bicolor (L.) Moench] varieties used in Burkina Faso showed that they have different contents of phenolic compounds, peroxidase (POX), and polyphenol oxidase (PPO). Most of the varieties (82%) had a tannin content less than 0.25% (w/w). POX specific activity was higher than the monophenolase and o-diphenolase specific activities of PPO. For POX, there was a diversity of isoforms among varieties. No clear correlation could be made between the quantitative composition of the grain in phenolics, PPO, and POX, and resistance of plant to pathogens. In general, varieties good for a thick porridge preparation ("tô") had low phenolic compounds content and a medium POX activity. From the red varieties, those used for local beer ("dolo") had a high content in phenolic compounds and PPO, and a low POX activity. The variety considered good for couscous had a low POX content. The characteristics might be useful as selection markers for breeding for specific applications.

Variation of anthocyanins and other major phenolic compounds throughout the ripening of four Portuguese blueberry (Vaccinium corymbosum L) cultivars.

PubMed

Silva, Sara; Costa, Eduardo M; Coelho, Marta C; Morais, Rui M; Pintado, Manuela E

2017-01-01

Blueberries are widely recognised as one of the richest sources of bioactive compounds, among which are anthocyanins, though the ripeness of berries has been reported as affecting the phytochemical composition of fruits. Therefore, the present work aimed to evaluate the variation of anthocyanins, and other major phenolics, throughout five ripening stages in four blueberry cultivars. The results showed that the antioxidant capacity and anthocyanin content increased during ripening, reaching the highest values when the blueberries are collected from bunches comprised of 75% ripe blueberries. Antagonistically, the amount of phenolic acid decreases, while the quercetin-3-glucoside levels remain stable. Furthermore, Goldtraube blueberries appear to possess, systematically, higher amounts of phenolic compounds than the other cultivars studied. Thus, when seeking the highest yield of anthocyanins, the preferred harvest should occur in bunches that contain ca 75% of ripe blueberries and, considering the cultivars assayed, the Goldtraube cultivar appears to be the richest in phenolic compounds.

Inhibition of the acetoclastic methanogenic activity by phenol and alkyl phenols.

PubMed

Olguin-Lora, P; Puig-Grajales, L; Razo-Flores, E

2003-08-01

Chemical and petrochemical industries are important sources of aromatic pollutants. Petrochemical processes like caustic washing of middle distillates produce the spent caustic liquors highly concentrated in phenol and alkyl phenols. The anaerobic technology is considered a feasible strategy for petrochemical wastewater pre-treatment although high concentrations of phenol could limit its efficiency. The goal of this work was to determine the toxicity of both selected alkyl phenols and a synthetic "spent-caustic phenols mixture" on the acetoclastic Specific Methanogenic Activity (SMA) of unadapted and phenol-adapted granular sludge. Alkyl phenols were responsible for 50% (IC50) and 100% (IC100) inhibition of the SMA at concentrations ranging from 1.6 to 5.0 mM and from 4.1 to 27.5 mM, respectively, for un-adapted granular sludge. In the case of phenol-adapted granular sludge, the inhibitory concentrations ranged from 1.7 to 14.9 mM and from 4.0 to 83.0 for IC50 and IC100, respectively, highlighting the impact of sludge acclimation. The inhibition produced by 2-ethylphenol was more acute compared to phenol and was not reduced by the phenol acclimation process. The IC50 and IC100 values obtained for the synthetic "spent-caustic phenols mixture" were 9.5 mM and 88.4 mM, respectively. The inhibitory concentrations of phenol compounds were closely correlated with compound apolarity (log P), indicating that the lipophilic character of the tested compounds was responsible for their methanogenic toxicity. An inhibition model is confirmed to estimate the IC50 and IC100.

Profiling of phenolic compounds and antioxidant properties of European varieties and cultivars of Vicia faba L. pods.

PubMed

Valente, Inês M; Maia, Margarida R G; Malushi, Nertila; Oliveira, Hugo M; Papa, Lumturi; Rodrigues, José A; Fonseca, António J M; Cabrita, Ana R J

2018-08-01

Vicia faba L. pods are a by-product generated from the industrial processing of beans for human and animal consumption. As phenolic compounds may play important roles in health, the present work envisaged the phenolic characterization of seven European varieties and cultivars of V. faba (major and minor) pods and the assessment of their antioxidant activity. The V. faba methanolic extracts were characterized by HPLC-DAD-MS/MS for identification of polyphenolic compounds. The total phenolic content and antioxidant capacity of the extracts were evaluated by colorimetric methods (Folin-Ciocalteu, DPPH scavenging capacity assay, and FRAP assay). Main compounds identified by HPLC-DAD-MS/MS were derivatives of caffeic acid, coumaric acid and kaempferol. The broad bean Jögeva variety presented the highest content of free and esterified phenolics (26.3 and 26.7 mg 100 g -1 dry weight, respectively), followed by the horse bean varieties Bauska and Lielplatones. These results were corroborated by the analysis of total phenolic content, DPPH scavenging capacity and FRAP. This study confirmed the rich phenolic content of V. faba pods suggesting to be an interesting novel source for animal nutrition, promoting product quality and consumers' health. Copyright © 2018 Elsevier Ltd. All rights reserved.

Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation

PubMed Central

García-Martínez, Olga; De Luna-Bertos, Elvira; Ramos-Torrecillas, Javier; Ruiz, Concepción; Milia, Egle; Lorenzo, María Luisa; Jimenez, Brigida; Sánchez-Ortiz, Araceli; Rivas, Ana

2016-01-01

In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11–16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18–22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9–13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly. PMID:26930190

Imperanene, a novel phenolic compound with platelet aggregation inhibitory activity from Imperata cylindrica.

PubMed

Matsunaga, K; Shibuya, M; Ohizumi, Y

1995-01-01

Imperanene, a novel phenolic compound [1] has been isolated from Imperata cylindrica. Its structure was elucidated by spectroscopic evidence. Imperanene showed platelet aggregation inhibitory activity.

The Potential Protective Effects of Phenolic Compounds against Low-density Lipoprotein Oxidation.

PubMed

Amarowicz, Ryszard; Pegg, Ronald B

2017-01-01

The exact mechanism(s) of atherosclerosis in humans remains elusive, but one theory hypothesizes that this deleterious process results from the oxidative modification of low-density lipoprotein (LDL). Research suggests that foods rich in dietary phenolic compounds with antioxidant activity can mitigate the extent of LDL oxidation in vivo. With regard to the different classes of flavonoids, there appears to be a structurefunction relationship between the various moieties/constituents attached to the flavonoids' three ring system and their impact at retarding LDL oxidation. This article summarizes the findings to date of both in vitro and in vivo studies using foods or phenolic extracts isolated from foodstuffs at inhibiting the incidence of LDL oxidation. Three bases: SCOPUS, Web Science, and PubMed were used for search. An often used method for the determination of antioxidant properties of natural phenolic compounds is the LDL oxidation assay. LDLs are isolated from human plasma and their oxidation is induced by Cu2+ ions or 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH). The sample is incubated with a phenolic extract or individual/isolated phenolic compounds. LDL oxidation is then monitored by various chemical methods (e.g., measurement of the generation of conjugated dienes and trienes). This technique confirmed the antioxidant properties of several extracts as obtained from plant material (e.g., grapes, berries, orange, grapefruit, coffee, tea, chocolate, olives, nuts) as well as the individual phenolic compounds (e.g., luteolinidin, apigenidin, caffeic acid, chlorogenic acid, catechin, quercetin, rutin). Several studies in vivo confirmed protective effects of phenolic compounds against LDL oxidation. They covered the healthy subjects with hyperlipidaemia, overweight, obesity, metabolic syndrome, heavy smokers, patients receiving haemodialysis, patients with peripheral vascular disease, and subjects at high cardiovascular risk. The studies comprise individuals of all ages, and the number of participants in the different experiments varied widely. Properly designed double-blind, placebo-controlled randomised clinical trials offer stronger evidence as to the impact of dietary phenolics consumption at retarding LDL oxidation. More such clinical trials are needed to strengthen the hypothesis that foods rich in dietary phenolic compounds with antioxidant activity can mitigate the extent of LDL oxidation in vivo. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Purple Corn (Zea mays L.) Phenolic Compounds Profile and Its Assessment as an Agent Against Oxidative Stress in Isolated Mouse Organs

PubMed Central

Ramos-Escudero, Fernando; Muñoz, Ana María; Alvarado-Ortíz, Carlos; Alvarado, Ángel

2012-01-01

Abstract This study was designed to determine the contents of total polyphenols, flavonoids, flavonols, flavanols, and anthocyanins of purple corn (Zea mays L.) extracts obtained with different methanol:water concentrations, acidified with 1% HCl (1 N). Another objective was to determine the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ferric reducing antioxidant power (FRAP), and deoxyribose assay, individual phenolic compounds by high-performance liquid chromatography (HPLC), and endogenous antioxidant enzyme (superoxide dismutase [SOD], catalase [CAT], and total peroxidase [TPX]) activity and lipid peroxidation activity (thiobarbituric acid–reactive substances [TBARS] assay) in isolated mouse organs. Overall, the highest total content of polyphenols, anthocyanins, flavonoids, flavonols, and flavanols was obtained with the 80:20 methanol:water extract, acidified with 1% HCl (1 N). The 50% inhibitory concentration values obtained by the DPPH and ABTS assays with this extract were 66.3 μg/mL and 250 μg/mL, respectively. The antioxidant activity by the FRAP assay was 26.1 μM Trolox equivalents/g, whereas the deoxyribose assay presented 93.6% inhibition. Because of these results, the 80:20 methanol:water extract, acidified with 1% HCl (1 N), was used for the remaining tests. Eight phenolic compounds were identified by HPLC: chlorogenic acid, caffeic acid, rutin, ferulic acid, morin, quercetin, naringenin, and kaempferol. Furthermore, it was observed that the purple corn extract was capable of significantly reducing lipid peroxidation (lower malondialdehyde [MDA] concentrations by the TBARS assay) and at the same time increasing endogenous antioxidant enzyme (CAT, TPX, and SOD) activities in isolated mouse kidney, liver, and brain. On the basis of the results, it was concluded that the purple corn extract contained various bioactive phenolic compounds that exhibited considerable in vitro antioxidant activity, which correlated well with the decreased MDA formation and increase in activity of endogenous antioxidant enzymes observed in the isolated mouse organs. This warrants further in vivo studies with purple corn extracts to assess its antioxidant activity and other bioactivities. PMID:22082063

Purple corn (Zea mays L.) phenolic compounds profile and its assessment as an agent against oxidative stress in isolated mouse organs.

PubMed

Ramos-Escudero, Fernando; Muñoz, Ana María; Alvarado-Ortíz, Carlos; Alvarado, Ángel; Yáñez, Jaime A

2012-02-01

This study was designed to determine the contents of total polyphenols, flavonoids, flavonols, flavanols, and anthocyanins of purple corn (Zea mays L.) extracts obtained with different methanol:water concentrations, acidified with 1% HCl (1 N). Another objective was to determine the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ferric reducing antioxidant power (FRAP), and deoxyribose assay, individual phenolic compounds by high-performance liquid chromatography (HPLC), and endogenous antioxidant enzyme (superoxide dismutase [SOD], catalase [CAT], and total peroxidase [TPX]) activity and lipid peroxidation activity (thiobarbituric acid-reactive substances [TBARS] assay) in isolated mouse organs. Overall, the highest total content of polyphenols, anthocyanins, flavonoids, flavonols, and flavanols was obtained with the 80:20 methanol:water extract, acidified with 1% HCl (1 N). The 50% inhibitory concentration values obtained by the DPPH and ABTS assays with this extract were 66.3 μg/mL and 250 μg/mL, respectively. The antioxidant activity by the FRAP assay was 26.1 μM Trolox equivalents/g, whereas the deoxyribose assay presented 93.6% inhibition. Because of these results, the 80:20 methanol:water extract, acidified with 1% HCl (1 N), was used for the remaining tests. Eight phenolic compounds were identified by HPLC: chlorogenic acid, caffeic acid, rutin, ferulic acid, morin, quercetin, naringenin, and kaempferol. Furthermore, it was observed that the purple corn extract was capable of significantly reducing lipid peroxidation (lower malondialdehyde [MDA] concentrations by the TBARS assay) and at the same time increasing endogenous antioxidant enzyme (CAT, TPX, and SOD) activities in isolated mouse kidney, liver, and brain. On the basis of the results, it was concluded that the purple corn extract contained various bioactive phenolic compounds that exhibited considerable in vitro antioxidant activity, which correlated well with the decreased MDA formation and increase in activity of endogenous antioxidant enzymes observed in the isolated mouse organs. This warrants further in vivo studies with purple corn extracts to assess its antioxidant activity and other bioactivities.

Effect of processing on phenolic acids composition and radical scavenging capacity of barley pasta.

PubMed

De Paula, Rosanna; Rabalski, Iwona; Messia, Maria Cristina; Abdel-Aal, El-Sayed M; Marconi, Emanuele

2017-12-01

Phenolic acids, total phenolics content and DPPH radical scavenging capacity in raw ingredients, fresh and dried spaghetti, and in uncooked and cooked spaghetti were evaluated and compared with semolina spaghetti as a reference. Ferulic acid was the major phenolic acid found in the free and bound phenolic extracts in all the investigated pasta samples. The addition of barley flour into pasta at incorporation levels of 30, 50 and 100% increased phenolic acids and total phenolics content. Pasta processing did not significantly affect the total phenolics content and free radical scavenging capacity, but a significant reduction in total phenolic acids measured by HPLC was found. Drying process differently affected individual phenolic compounds in the free and bound fractions, and thus, the total phenolic acids content. Free vanillic, caffeic and p-coumaric acids did not significantly change, while p-hydroxybenzoic and ferulic acids of the free extracts showed higher values compared to the corresponding fresh pasta. Cooking did not greatly affect total phenolic acids, more leading to conserving free and bound phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Profiling polyphenol composition by HPLC-DAD-ESI/MSn and the antibacterial activity of infusion preparations obtained from four medicinal plants.

PubMed

Ziani, Borhane E C; Barros, Lillian; Boumehira, Ali Z; Bachari, Khaldoun; Heleno, Sandrina A; Alves, Maria Jose; Ferreira, Isabel C F R

2018-01-24

The infusions of Thymus pallescens Noë, Saccocalyx satureioides Coss. et Dur., Ptychotis verticillata Briq. and Limoniastrum guyonianum Boiss. have been used as medicinal remedies for many diseases in Algerian folk medicine. These species have also been well documented as rich sources of phytochemicals, such as phenolic compounds with wide diversified chemical structures, which exhibit far-ranging biological activities. Thus, the phenolic compound profile of the aqueous extracts, obtained by infusing, of the mentioned species was obtained by HPLC-DAD-ESI/MS, and their antibacterial activity was evaluated against clinical isolates. Several phenolic acids were identified and quantified, particularly caffeic acid derivatives along with glycosylated flavonoids. T. pallescens and S. satureioides contain 13 phenolic compounds, where rosmarinic acid was the most abundant phenolic acid present, while L. guyonianum presented myricetin-3-O-glucoside and myricetin-O-rhamnoside as the main compounds among the eight detected molecules. P. verticillata presented a profile of ten phenolic compounds, where 5-O-caffeoylquinic acid was the most abundant phenolic acid, followed by the flavone luteolin-3-O-glucoside. The antibacterial activity of the infusions ranged between 2.5 and 20 mg mL -1 (MIC values), and L. guyonianum showed the highest activity against all of the tested bacteria, Staphylococcus aureus and Pseudomonas aeruginosa being the most sensitive and resistant strains, respectively. Thus, the studied plant species are sources of natural antibacterial substances that can be used to fight against pathogenic microorganisms.

Enhancement of Phenolic Production and Antioxidant Activity from Buckwheat Leaves by Subcritical Water Extraction.

PubMed

Kim, Dong-Shin; Kim, Mi-Bo; Lim, Sang-Bin

2017-12-01

To enhance the production of phenolic compounds with high antioxidant activity and reduce the level of phototoxic fagopyrin, buckwheat leaves were extracted with subcritical water (SW) at 100~220°C for 10~50 min. The major phenolic compounds were quercetin, gallic acid, and protocatechuic acid. The cumulative amount of individual phenolic compounds increased with increasing extraction temperature from 100°C to 180°C and did not change significantly at 200°C and 220°C. The highest yield of individual phenolic compounds was 1,632.2 μg/g dry sample at 180°C, which was 4.7-fold higher than that (348.4 μg/g dry sample) at 100°C. Total phenolic content and total flavonoid content increased with increasing extraction temperature and decreased with increasing extraction time, and peaked at 41.1 mg gallic acid equivalents/g and 26.9 mg quercetin equivalents/g at 180°C/10 min, respectively. 2,2-Diphenyl-1-picrylhydrazyl free radical scavenging activity and ferric reducing ability of plasma reached 46.4 mg ascorbic acid equivalents/g and 72.3 mmol Fe 2+ /100 g at 180°C/10 min, respectively. The fagopyrin contents were reduced by 92.5~95.7%. Color values L * and b * decreased, and a * increased with increasing extraction temperature. SW extraction enhanced the yield of phenolic compounds with high antioxidant activity and reduced the fagopyrin content from buckwheat leaves.

Application of HPLC and ESI-MS techniques in the analysis of phenolic acids and flavonoids from green leafy vegetables (GLVs).

PubMed

Kumar, B Ramesh

2017-12-01

Diets containing high proportions of fruits and vegetables reduce the risk of onset of chronic diseases. The role of herbal medicines in improving human health is gaining popularity over the years, which also increases the need for safety and efficiency of these products. Green leafy vegetables (GLVs) are the richest source of phenolic compounds with excellent antioxidant properties. Increased consumption of diets containing phenolic compounds may give positive and better results to human health and significantly improves the immune system. Highly selective, susceptible and versatile analytical techniques are necessary for extraction, identification, and quantification of phenolic compounds from plant extracts, which helps to utilize their important biological properties. Recent advances in the pre-treatment procedures, separation techniques and spectrometry methods are used for qualitative and quantitative analysis of phenolic compounds. The online coupling of liquid chromatography with mass spectrometry (LC-MS) has become a useful tool in the metabolic profiling of plant samples. In this review, the separation and identification of phenolic acids and flavonoids from GLVs by LC-MS have been discussed along with the general extraction procedures and other sources of mass spectrometer used. The review is devoted to the understanding of the structural configuration, nature and accumulation pattern of phenolic acids and flavonoids in plants and to highlighting the recent developments in the chemical investigation of these compounds by chromatographic and spectroscopic techniques. It concludes with the advantages of the combination of these two methods and prospects.

The roles of plant phenolics in defence and communication during Agrobacterium and Rhizobium infection.

PubMed

Bhattacharya, Amita; Sood, Priyanka; Citovsky, Vitaly

2010-09-01

Phenolics are aromatic benzene ring compounds with one or more hydroxyl groups produced by plants mainly for protection against stress. The functions of phenolic compounds in plant physiology and interactions with biotic and abiotic environments are difficult to overestimate. Phenolics play important roles in plant development, particularly in lignin and pigment biosynthesis. They also provide structural integrity and scaffolding support to plants. Importantly, phenolic phytoalexins, secreted by wounded or otherwise perturbed plants, repel or kill many microorganisms, and some pathogens can counteract or nullify these defences or even subvert them to their own advantage. In this review, we discuss the roles of phenolics in the interactions of plants with Agrobacterium and Rhizobium.

Liquid-liquid and solid-phase extractions of phenols from virgin olive oil and their separation by chromatographic and electrophoretic methods.

PubMed

Bendini, Alessandra; Bonoli, Matteo; Cerretani, Lorenzo; Biguzzi, Barbara; Lercker, Giovanni; Toschi, Tullia Gallina

2003-01-24

The high oxidative stability of virgin olive oil is related to its high monounsaturated/polyunsaturated ratio and to the presence of antioxidant compounds, such as tocopherols and phenols. In this paper, the isolation of phenolic compounds from virgin olive oil, by different methods, was tested and discussed. Particularly liquid-liquid and solid-phase extraction methods were compared, assaying, for the latter, three stationary phases (C8, C18 and Diol) and several elution mixtures. Quantification of phenolic and o-diphenolic substances in the extracts was performed by the traditional Folin-Ciocalteau method and the sodium molybdate reaction, respectively. Furthermore, the quantification of phenolic compounds in the extracts and in a standard mixture was carried out both with diode array and mass spectrometric detection and capillary zone electrophoresis.

Interactions between wine phenolic compounds and human saliva in astringency perception.

PubMed

García-Estévez, Ignacio; Ramos-Pineda, Alba María; Escribano-Bailón, María Teresa

2018-03-01

Astringency is a complex perceptual phenomenon involving several sensations that are perceived simultaneously. The mechanism leading to these sensations has been thoroughly and controversially discussed in the literature and it is still not well understood since there are many contributing factors. Although we are still far from elucidating the mechanisms whereby astringency develops, the interaction between phenolic compounds and proteins (from saliva, oral mucosa or cells) seems to be most important. This review summarizes the recent trends in the protein-phenol interaction, focusing on the effect of the structure of the phenolic compound on the interaction with salivary proteins and on methodologies based on these interactions to determine astringency.

Analysis of phenolic compounds for poultry feed by supercritical fluid chromatography

USDA-ARS?s Scientific Manuscript database

Phenolic compounds have generated interest as components in functional feed formulations due to their anti-oxidant, anti-microbial, and anti-fungal properties. These compounds may have greater significance in the future as the routine use of antibiotics is reduced and the prevalence of resistant bac...

Postharvest changes in the phenolic profile of watercress induced by post-packaging irradiation and modified atmosphere packaging.

PubMed

Pinela, José; Barros, Lillian; Barreira, João C M; Carvalho, Ana Maria; Oliveira, M Beatriz P P; Santos-Buelga, Celestino; Ferreira, Isabel C F R

2018-07-15

The effects of γ-ray irradiation and modified atmosphere packaging (MAP) on watercress (Nasturtium officinale R. Br.) phenolic compounds were evaluated after 7-day storage at 4 °C. Irradiation doses of 1, 2 and 5 kGy were tested, as well as vacuum-packaging and MAP enriched with 100% N 2 and Ar. A non-irradiated, air-packaged control was included in all experiments. p-Coumaric acid was the most abundant compound in fresh watercress, followed by quercetin-3-O-sophoroside and isorhamnetin-O-hydroxyferuloylhexoside-O-hexoside. Four kaempferol glycoside derivatives were identified for the first time in this species. In general, flavonoids predominated over phenolic acids. Samples stored under vacuum and irradiated at 2 kGy revealed lower phenolic levels. Ar-enriched MAP and control conditions preserved the initial phenolic content. The 5 kGy dose also maintained concentrations of flavonoids and total phenolic compounds, but increased the phenolic acids content. Additionally, flavonoids were found strongly correlated to DPPH scavenging activity and β-carotene bleaching inhibition capacity. Copyright © 2018 Elsevier Ltd. All rights reserved.

Determination of some phenolic compounds in red wine by RP-HPLC: method development and validation.

PubMed

Burin, Vívian Maria; Arcari, Stefany Grützmann; Costa, Léa Luzia Freitas; Bordignon-Luiz, Marilde T

2011-09-01

A methodology employing reversed-phase high-performance liquid chromatography (RP-HPLC) was developed and validated for simultaneous determination of five phenolic compounds in red wine. The chromatographic separation was carried out in a C(18) column with water acidify with acetic acid (pH 2.6) (solvent A) and 20% solvent A and 80% acetonitrile (solvent B) as the mobile phase. The validation parameters included: selectivity, linearity, range, limits of detection and quantitation, precision and accuracy, using an internal standard. All calibration curves were linear (R(2) > 0.999) within the range, and good precision (RSD < 2.6%) and recovery (80-120%) was obtained for all compounds. This method was applied to quantify phenolics in red wine samples from Santa Catarina State, Brazil, and good separation peaks for phenolic compounds in these wines were observed.

The content of phenolic compounds in leaf tissues of Aesculus glabra and Aesculus parviflora walt.

PubMed

Oszmiański, Jan; Kolniak-Ostek, Joanna; Biernat, Agata

2015-01-28

In plants, flavonoids play an important role in biological processes. They are involved in UV-scavenging, fertility and disease resistance. Therefore, in this study, we attempted to quantify and characterize phenolic compounds in Aesculus parviflora Walt. leaves and Aesculus glabra leaves partly suffering from attack by a leaf mining insect (C. ohridella). A total of 28 phenolic compounds belonging to the hydroxycinnamic acid, flavan-3-ols and flavonol groups were identified and quantified in Aesculus parviflora and A. glabra leaf extracts. Significantly decreased concentrations of some phenolic compounds, especially of flavan-3-ols, were observed in infected leaves compared to the non-infected ones. Additionally, a higher content of polymeric procyanidins in leaves of Aesculus parviflora than in Aesculus glabra may explain their greater resistance to C. ohridella insects.

Mixture-amount design and response surface modeling to assess the effects of flavonoids and phenolic acids on developmental performance of Anastrepha ludens.

PubMed

Pascacio-Villafán, Carlos; Lapointe, Stephen; Williams, Trevor; Sivinski, John; Niedz, Randall; Aluja, Martín

2014-03-01

Host plant resistance to insect attack and expansion of insect pests to novel hosts may to be modulated by phenolic compounds in host plants. Many studies have evaluated the role of phenolics in host plant resistance and the effect of phenolics on herbivore performance, but few studies have tested the joint effect of several compounds. Here, we used mixture-amount experimental design and response surface modeling to study the effects of a variety of phenolic compounds on the development and survival of Mexican fruit fly (Anastrepha ludens [Loew]), a notorious polyphagous pest of fruit crops that is likely to expand its distribution range under climate change scenarios. (+)- Catechin, phloridzin, rutin, chlorogenic acid, and p-coumaric acid were added individually or in mixtures at different concentrations to a laboratory diet used to rear individuals of A. ludens. No effect was observed with any mixture or concentration on percent pupation, pupal weight, adult emergence, or survival from neonate larvae to adults. Larval weight, larval and pupal developmental time, and the prevalence of adult deformities were affected by particular mixtures and concentrations of the compounds tested. We suggest that some combinations/concentrations of phenolic compounds could contribute to the management of A. ludens. We also highlight the importance of testing mixtures of plant secondary compounds when exploring their effects upon insect herbivore performance, and we show that mixture-amount design is a useful tool for this type of experiments.

A modification of the Hammett equation for predicting ionisation constants of p-vinyl phenols.

PubMed

Sipilä, Julius; Nurmi, Harri; Kaukonen, Ann Marie; Hirvonen, Jouni; Taskinen, Jyrki; Yli-Kauhaluoma, Jari

2005-01-01

Currently there are several compounds used as drugs or studied as new chemical entities, which have an electron withdrawing group connected to a vinylic double bond in a phenolic or catecholic core structure. These compounds share a common feature--current computational methods utilizing the Hammett type equation for the prediction of ionisation constants fail to give accurate prediction of pK(a)'s for compounds containing the vinylic moiety. The hypothesis was that the effect of electron-withdrawing substituents on the pK(a) of p-vinyl phenols is due to the delocalized electronic structure of these compounds. Thus, this effect should be additive for multiple substituents attached to the vinylic double bond and quantifiable by LFER-based methods. The aim of this study was to produce an improved equation with a reduced tendency to underestimate the effect of the double bond on the ionisation of the phenolic hydroxyl. To this end a set of 19 para-substituted vinyl phenols was used. The ionisation constants were measured potentiometrically, and a training set of 10 compounds was selected to build a regression model (r2 = 0.987 and S.E. = 0.09). The average error with an external test set of six compounds was 0.19 for our model and 1.27 for the ACD-labs 7.0. Thus, we have been able to significantly improve the existing model for prediction of the ionisation constants of substituted p-vinyl phenols.

Mutagenicity testing in the Salmonella typhimurium assay of phenolic compounds and phenolic fractions obtained from smokehouse smoke condensates.

PubMed

Pool, B L; Lin, P Z

1982-08-01

Smokehouse smoke, which is used for flavouring meat products, was investigated for its mutagenic activity in the Salmonella typhimurium assay. We were chiefly concerned with the fractions free of polycyclic aromatic hydrocarbons but containing phenol compounds, which are responsible for the preservative and aromatizing properties of the smoke. The most abundantly occurring phenol compounds (phenol, cresols, 2,4-dimethylphenol, brenzcatechine, syringol, eugenol, vanilline and guaiacol) gave negative results when they were tested for mutagenicity at five concentrations up to 5000 micrograms/plate, with and without S-9 mix, using five strains of S. typhimurium. Even when phenol was further investigated in a variety of test conditions, no induction of his+ revertants was observed. When smokehouse smoke was condensed and fractionated the majority of the various phenolic fractions also gave negative results when tested at five concentrations using five strains of S. typhimurium. However there was a slight increase in the number of revertants in a few cases. The presence in the phenolic fractions of very small amounts of mutagenic impurities, the nature of which needs further investigation, cannot be excluded. These results support the further development of non-hazardous smoke-aroma preparations, based on the phenolic components of smokehouse smoke.

Bean cultivars (Phaseolus vulgaris L.) have similar high antioxidant capacity, in vitro inhibition of alpha-amylase and alpha-glucosidase while diverse phenolic composition and concentration

USDA-ARS?s Scientific Manuscript database

Common beans are a good source of essential nutrients such as protein, fiber, vitamins, and minerals; they also contain phenolic compounds and other phytochemicals. Phenolic compounds exhibit high antioxidant capacity that promotes health benefits by reducing oxidative stress. The objective was to c...

Identification and quantification of phenolic compounds of selected fruits from Madeira Island by HPLC-DAD-ESI-MS(n) and screening for their antioxidant activity.

PubMed

Spínola, Vítor; Pinto, Joana; Castilho, Paula C

2015-04-15

Five fruits species commonly cultivated and consumed in Madeira Island (Portugal) were investigated for their phenolic profile by means of reversed phase high-performance liquid chromatography coupled to diode array detection and electrospray ionisation mass spectrometry (HPLC-DAD-ESI/MS(n)) and antioxidant potential. A large number of compounds were characterised, flavonoids and phenolic acids being the major components found in target samples, 39 compounds (flavonoids, phenolic acids, terpenoids, cyanogenic glycosides and organic acids) were identified in cherimoyas, lemons, papayas, passion-fruits and strawberries for the first time. Furthermore, all samples were systematically analysed for their total phenolic and flavonoid contents along with two radical scavenging methods (ABTS and ORAC) for antioxidant activity measurement. Target fruits presented high phenolic contents which is responsible for most of the antioxidant activity against radical reactive species (R(2)>0.80). Quantitative data showed that anthocyanins, in particular pelargonidin-3-O-hexoside (>300 mg/100 mL), present only in strawberries were the compounds in largest amounts but are the ones which contribute less to the antioxidant activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Tea and coffee time with bacteria - Investigation of uptake of key coffee and tea phenolics by wild type E. coli.

PubMed

Hakeem Said, Inamullah; Gencer, Selin; Ullrich, Matthias S; Kuhnert, Nikolai

2018-06-01

Dietary phenolic compounds are often transformed by gut microbiota prior to absorption. This transformation may modulate their biological activities. Many fundamental questions still need to be addressed to understand how the gut microbiota-diet interactions affect human health. Herein, a UHPLC-QTOF mass spectrometry-based method for the quantification of uptake and determination of intracellular bacterial concentrations of dietary phenolics from coffee and tea was developed. Quantitative uptake data for selected single purified phenolics were determined. The specific uptake from mixtures containing up to four dietary relevant compounds was investigated to assess changes of uptake parameters in a mixture model system. Indeed, perturbation of bacteria by several compounds alters uptake parameter in particular t max . Finally, model bacteria were dosed with complex dietary mixtures such as diluted tea or coffee extracts. The uptake kinetics of the twenty most abundant phenolics was quantified and the findings are discussed. For the first time, quantitative data on in-vitro uptake of dietary phenolics from food matrices were obtained indicating a time-dependent differential uptake of nutritional compounds. Copyright © 2018. Published by Elsevier Ltd.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat.

PubMed

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat

PubMed Central

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

Effect of In Vitro Digestion on the Total Antioxidant Capacity and Phenolic Content of 3 Species of Oregano (Hedeoma patens, Lippia graveolens, Lippia palmeri).

PubMed

Gutiérrez-Grijalva, Erick Paul; Angulo-Escalante, Miguel Angel; León-Félix, Josefina; Heredia, J Basilio

2017-12-01

Oregano phenolic compounds have been studied for their anti-inflammatory properties. Nonetheless, after ingestion, the gastrointestinal environment can affect their antioxidant stability and thus their bioactive properties. To evaluate the effect of in vitro gastrointestinal (GI) digestion on the phenolic compounds of 3 species of oregano (Hedeoma patens, Lippia graveolens, and Lippia palmeri), the total reducing capacity, total flavonoid content, and antioxidant capacity were evaluated before and after in vitro GI digestion. In addition, the phenolic compounds of the 3 oregano species were identified and quantified by UPLC-PDA before and after in vitro GI digestion. It was shown that the reducing capacity, flavonoid content and antioxidant capacity were affected by the GI digestion process. Moreover, the phenolic compounds identified were apigenin-7-glucoside, scutellarein, luteolin, luteolin-7-glucoside, phloridzin and chlorogenic acid, and their levels were affected by the in vitro GI process. Our results showed that the phenolic compounds from these 3 species of oregano are affected by the in vitro digestion process, and this effect is largely attributable to pH changes. These changes can modify the bioavailability and further anti-inflammatory activity of oregano phenolics, and thus, further research is needed. Oregano is a rich source of polyphenols that have shown bioactive properties like anti-inflammatory potential. However, little is known of the gastrointestinal fate of oregano polyphenols which is imperative to fully understand its bioaccessibility. Our results are important to develop new administration strategies which could help protect the antioxidant and anti-inflammatory potential and bioaccessibility of such compounds. © 2017 Institute of Food Technologists®.

Brazilian Capsicum peppers: capsaicinoid content and antioxidant activity.

PubMed

Bogusz, Stanislau; Libardi, Silvia H; Dias, Fernanda Fg; Coutinho, Janclei P; Bochi, Vivian C; Rodrigues, Daniele; Melo, Arlete Mt; Godoy, Helena T

2018-01-01

Capsicum peppers are known as a source of capsaicinoids, phenolic compounds and antioxidants. Brazilian Capsicum peppers are important spices used in foods worldwide. However, little information is available on the chemical composition and antioxidant activity of these peppers. Capsaicin, dihydrocapsaicin, total phenolic compounds and antioxidant activity were investigated in extracts of three Brazilian peppers: Capsicum frutescens, C. chinense and C. baccatum var. pendulum, in two different harvest years and at two ripening stages. The bioactive compound content was dependent on harvest year, and changes in the concentration profiles were found for capsaicin. Mature fruits of C. chinense harvested in the first year had the highest capsaicin concentration (2.04 mg g -1 fresh pepper), and mature fruits of C. frutescens harvested in the same first year had the highest dihydrocapsaicin content (0.95 mg g -1 fresh pepper). Mature fruits of C. frutescens harvested in the first year showed the major total phenolic compound content (2.46 mg g -1 fresh pepper). The total phenolic compound content was directly related to antioxidant activity. Our results suggest that phenolic compounds significantly contribute to the antioxidant activity of the investigated peppers. Also, these data add valued novel information that enhances current knowledge of Brazilian pepper fruits. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Absorption Profile of (Poly)Phenolic Compounds after Consumption of Three Food Supplements Containing 36 Different Fruits, Vegetables, and Berries

PubMed Central

Bresciani, Letizia; Martini, Daniela; Mena, Pedro; Tassotti, Michele; Calani, Luca; Brigati, Giacomo; Brighenti, Furio; Holasek, Sandra; Malliga, Daniela-Eugenia; Lamprecht, Manfred; Del Rio, Daniele

2017-01-01

The market of plant-based nutraceuticals and food supplements is continuously growing due to the increased consumer demand. The introduction of new products with relevant nutritional characteristics represents a new way of providing bioactive compounds and (poly)phenols to consumers, becoming a strategy to ideally guarantee the health benefits attributed to plant foodstuffs and allowing the increase of daily bioactive compound intake. A paramount step in the study of nutraceuticals is the evaluation of the bioavailability and metabolism of their putatively active components. Therefore, the aim of the present study was to investigate the absorption profile of the (poly)phenolic compounds contained in three different plant-based food supplements, made of 36 different plant matrices, which were consumed by 20 subjects in an open one-arm study design. Blood samples were collected at baseline and 1, 2, 5, and 10 h after capsule intake. Twenty quantifiable metabolites deriving from different (poly)phenolic compounds were identified. Results showed that the consumption of the three capsules allowed the effective absorption of several (poly)phenolic compounds and metabolites appearing at different times in plasma, thereby indicating different absorption profiles. The capsules thus ensured potential health-promoting molecules to be potentially available to target tissues and organs. PMID:28245627

Use of advanced techniques for the extraction of phenolic compounds from Tunisian olive leaves: phenolic composition and cytotoxicity against human breast cancer cells.

PubMed

Taamalli, Amani; Arráez-Román, David; Barrajón-Catalán, Enrique; Ruiz-Torres, Verónica; Pérez-Sánchez, Almudena; Herrero, Miguel; Ibañez, Elena; Micol, Vicente; Zarrouk, Mokhtar; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

2012-06-01

A comparison among different advanced extraction techniques such as microwave-assisted extraction (MAE), supercritical fluid extraction (SFE) and pressurized liquid extraction (PLE), together with traditional solid-liquid extraction, was performed to test their efficiency towards the extraction of phenolic compounds from leaves of six Tunisian olive varieties. Extractions were carried out at the best selected conditions for each technique; the obtained extracts were chemically characterized using high-performance liquid chromatography (HPLC) coupled to electrospray time-of-flight mass spectrometry (ESI-TOF-MS) and electrospray ion trap tandem mass spectrometry (ESI-IT-MS(2)). As expected, higher extraction yields were obtained for PLE while phenolic profiles were mainly influenced by the solvent used as optimum in the different extraction methods. A larger number of phenolic compounds, mostly of a polar character, were found in the extracts obtained by using MAE. Best extraction yields do not correlate with highest cytotoxic activity against breast cancer cells, indicating that cytotoxicity is highly dependent on the presence of certain compounds in the extracts, although not exclusively on a single compound. Therefore, a multifactorial behavior is proposed for the anticancer activity of olive leaf compounds. Copyright © 2012 Elsevier Ltd. All rights reserved.

Absorption Profile of (Poly)Phenolic Compounds after Consumption of Three Food Supplements Containing 36 Different Fruits, Vegetables, and Berries.

PubMed

Bresciani, Letizia; Martini, Daniela; Mena, Pedro; Tassotti, Michele; Calani, Luca; Brigati, Giacomo; Brighenti, Furio; Holasek, Sandra; Malliga, Daniela-Eugenia; Lamprecht, Manfred; Del Rio, Daniele

2017-02-26

The market of plant-based nutraceuticals and food supplements is continuously growing due to the increased consumer demand. The introduction of new products with relevant nutritional characteristics represents a new way of providing bioactive compounds and (poly)phenols to consumers, becoming a strategy to ideally guarantee the health benefits attributed to plant foodstuffs and allowing the increase of daily bioactive compound intake. A paramount step in the study of nutraceuticals is the evaluation of the bioavailability and metabolism of their putatively active components. Therefore, the aim of the present study was to investigate the absorption profile of the (poly)phenolic compounds contained in three different plant-based food supplements, made of 36 different plant matrices, which were consumed by 20 subjects in an open one-arm study design. Blood samples were collected at baseline and 1, 2, 5, and 10 h after capsule intake. Twenty quantifiable metabolites deriving from different (poly)phenolic compounds were identified. Results showed that the consumption of the three capsules allowed the effective absorption of several (poly)phenolic compounds and metabolites appearing at different times in plasma, thereby indicating different absorption profiles. The capsules thus ensured potential health-promoting molecules to be potentially available to target tissues and organs.

Redox Chemistry in Laccase-Catalyzed Oxidation of N-Hydroxy Compounds

PubMed Central

Xu, Feng; Kulys, Juozas J.; Duke, Kyle; Li, Kaichang; Krikstopaitis, Kastis; Deussen, Heinz-Josef W.; Abbate, Eric; Galinyte, Vilija; Schneider, Palle

2000-01-01

1-Hydroxybenzotriazole, violuric acid, and N-hydroxyacetanilide are three N-OH compounds capable of mediating a range of laccase-catalyzed biotransformations, such as paper pulp delignification and degradation of polycyclic hydrocarbons. The mechanism of their enzymatic oxidation was studied with seven fungal laccases. The oxidation had a bell-shaped pH-activity profile with an optimal pH ranging from 4 to 7. The oxidation rate was found to be dependent on the redox potential difference between the N-OH substrate and laccase. A laccase with a higher redox potential or an N-OH compound with a lower redox potential tended to have a higher oxidation rate. Similar to the enzymatic oxidation of phenols, phenoxazines, phenothiazines, and other redox-active compounds, an “outer-sphere” type of single-electron transfer from the substrate to laccase and proton release are speculated to be involved in the rate-limiting step for N-OH oxidation. PMID:10788380

Antimocrobial Polymer

DOEpatents

McDonald, William F.; Huang, Zhi-Heng; Wright, Stacy C.

2005-09-06

A polymeric composition having antimicrobial properties and a process for rendering the surface of a substrate antimicrobial are disclosed. The composition comprises a crosslinked chemical combination of (i) a polymer having amino group-containing side chains along a backbone forming the polymer, (ii) an antimicrobial agent selected from quaternary ammonium compounds, gentian violet compounds, substituted or unsubstituted phenols, biguanide compounds, iodine compounds, and mixtures thereof, and (iii) a crosslinking agent containing functional groups capable of reacting with the amino groups. In one embodiment, the polymer is a polyamide formed from a maleic anhydride or maleic acid ester monomer and alkylamines thereby producing a polyamide having amino substituted alkyl chains on one side of the polyamide backbone; the crosslinking agent is a phosphine having the general formula (A)3P wherein A is hydroxyalkyl; and the antimicrobial agent is chlorhexidine, dimethylchlorophenol, cetyl pyridinium chloride, gentian violet, triclosan, thymol, iodine, and mixtures thereof.

Bound Phenolics of Quinoa Seeds Released by Acid, Alkaline, and Enzymatic Treatments and Their Antioxidant and α-Glucosidase and Pancreatic Lipase Inhibitory Effects.

PubMed

Tang, Yao; Zhang, Bing; Li, Xihong; Chen, Peter X; Zhang, Hua; Liu, Ronghua; Tsao, Rong

2016-03-02

Unextractable phenolics from plant foods and their role in health benefits have become increasingly important. Meal residues of three quinoa seeds free of fat and extractable phenolics were subjected to acid, alkaline, and enzymatic hydrolyses. The total and individual phenolic compounds released were analyzed, and 19 phenolics, predominantly phenolic acids and several flavonoids, were identified. The concentration of bound phenolics was highest in black quinoa followed by red and white, regardless of the hydrolysis method. Higher phenolic contents also showed stronger antioxidant activities and inhibition of α-glucosidase and pancreatic lipase activities. Carbohydrases, that is, pectinase, xylanase and feruloyl esterase, which effectively liberated bound phenolics are known to be secreted by colonic bacteria, suggesting potential antioxidant and anti-inflammatory effects by these compounds in the large intestine during colonic fermentation. These results can also be applied to treat foods high in bound phenolics to enhance bioaccessibility.

Analysis of phenolic compounds from different morphological parts of Helichrysum devium by liquid chromatography with on-line UV and electrospray ionization mass spectrometric detection.

PubMed

Gouveia, Sandra C; Castilho, Paula C

2009-12-01

A simple and rapid method has been used for the screening and identification of the main phenolic compounds from Helichrysum devium using high-performance liquid chromatography with on-line UV and electrospray ionization mass spectrometric detection (LC-DAD/ESI-MS(n)). The total aerial parts and different morphological parts of the plant, namely leaves, flowers and stems, were analyzed separately. A total of 34 compounds present in the methanolic extract from Helichrysum devium were identified or tentatively characterized based on their UV and mass spectra and retention times. Three of these compounds were positively identified by comparison with reference standards. The phenolic compounds included derivatives of quinic acid, O-glycosylated flavonoids, a caffeic acid derivative and a protocatechuic acid derivative. The characteristic loss of 206 Da from malonylcaffeoyl quinic acid was used to confirm the malonyl linkage to the caffeoyl group. This contribution presents one of the first reports on the analysis of phenolic compounds from Helichrysum devium using LC-DAD/ESI-MS(n) and highlights the prominence of quinic acid derivatives as the main group of phenolic compounds present in these extracts. We also provide evidence that the methanolic extract from the flowers was significantly more complex when compared to that of other morphological parts. Copyright 2009 John Wiley & Sons, Ltd.

Antioxidant capacities and total phenolic contents increase with gamma irradiation in two types of Malaysian honey.

PubMed

Hussein, Saba Zuhair; Yusoff, Kamaruddin Mohd; Makpol, Suzana; Yusof, Yasmin Anum Mohd

2011-07-27

Two types of monofloral Malaysian honey (Gelam and Nenas) were analyzed to determine their antioxidant activities and total phenolic and flavonoid contents, with and without gamma irradiation. Our results showed that both types of honey can scavenge free radicals and exhibit high antioxidant-reducing power; however, Gelam honey exhibited higher antioxidant activity (p < 0.05) than Nenas honey, which is in good correlation (r = 0.9899) with its phenolic contents. Interestingly, we also noted that both irradiated honeys have higher antioxidant activities and total phenolic and flavonoid contents compared to nonirradiated honeys by Folin-Ciocalteu and UV-spectrophotometry methods, respectively. However, HPLC analysis for phenolic compounds showed insignificant increase between irradiated and nonirradiated honeys. The phenolic compounds such as: caffeic acid, chlorogenic acid, ellagic acid, p- coumaric acid, quercetin and hesperetin as indicated by HPLC method were found to be higher in Gelam honey versus Nenas honey. In conclusion, irradiation of honey causes enhanced antioxidant activities and flavonoid compounds.

Changes in Phenolic Compounds and Phytotoxicity of the Spanish-Style Green Olive Processing Wastewaters by Aspergillus niger B60.

PubMed

Papadaki, Eugenia; Tsimidou, Maria Z; Mantzouridou, Fani Th

2018-05-16

This study systematically investigated the degradation kinetics and changes in the composition of phenolic compounds in Spanish-style Chalkidiki green olive processing wastewaters (TOPWs) during treatment using Aspergillus niger B60. The fungal growth and phenol degradation kinetics were described sufficiently by the Logistic and Edward models, respectively. The maximum specific growth rate (2.626 1/d) and the maximum degradation rate (0.690 1/h) were observed at 1500 mg/L of total polar phenols, indicating the applicability of the process in TOPWs with a high concentration of phenolic compounds. Hydroxytyrosol and the other simple phenols were depleted after 3-8 days. The newly formed secoiridoid derivatives identified by HPLC-DAD-FLD and LC-MS are likely produced by oleoside and oleuropein aglycon via the action of fungal β-glucosidase and esterase. The treated streams were found to be less phytotoxic with reduced chemical oxygen demand by up to 76%. Findings will provide useful information for the subsequent treatment of residual contaminants.

Development of predictive models for total phenolics and free p-coumaric acid contents in barley grain by near-infrared spectroscopy.

PubMed

Han, Zhigang; Cai, Shengguan; Zhang, Xuelei; Qian, Qiufeng; Huang, Yuqing; Dai, Fei; Zhang, Guoping

2017-07-15

Barley grains are rich in phenolic compounds, which are associated with reduced risk of chronic diseases. Development of barley cultivars with high phenolic acid content has become one of the main objectives in breeding programs. A rapid and accurate method for measuring phenolic compounds would be helpful for crop breeding. We developed predictive models for both total phenolics (TPC) and p-coumaric acid (PA), based on near-infrared spectroscopy (NIRS) analysis. Regressions of partial least squares (PLS) and least squares support vector machine (LS-SVM) were compared for improving the models, and Monte Carlo-Uninformative Variable Elimination (MC-UVE) was applied to select informative wavelengths. The optimal calibration models generated high coefficients of correlation (r pre ) and ratio performance deviation (RPD) for TPC and PA. These results indicated the models are suitable for rapid determination of phenolic compounds in barley grains. Copyright © 2017 Elsevier Ltd. All rights reserved.

Phenolic Compounds of Cereals and Their Antioxidant Capacity.

PubMed

Van Hung, Pham

2016-01-01

Phenolic compounds play an important role in health benefits because of their highly antioxidant capacity. In this review, total phenolic contents (TPCs), phenolic acid profile and antioxidant capacity of the extracted from wheat, corn, rice, barley, sorghum, rye, oat, and millet, which have been recently reported, are summarized. The review shows clearly that cereals contain a number of phytochemicals including phenolics, flavonoids, anthocyanins, etc. The phytochemicals of cereals significantly exhibit antioxidant activity as measured by trolox equivalent antioxidant capacity (TEAC), 2,2-diphenyl-1-picrylhydrazyl radical scavenging, reducing power, oxygen radical absorbance capacity (ORAC), inhibition of oxidation of human low-density lipoprotein (LDL) cholesterol and DNA, Rancimat, inhibition of photochemilumenescence (PCL), and iron(II) chelation activity. Thus, the consumption of whole grains is considered to have significantly health benefits in prevention from chronic diseases such as cardiovascular disease, diabetes, and cancer because of the contribution of phenolic compounds existed. In addition, the extracts from cereal brans are considered to be used as a source of natural antioxidants.

Evaluating water deficit and glyphosate treatment on the accumulation of phenolic compounds and photosynthesis rate in transgenic Codonopsis lanceolata (Siebold & Zucc.) Trautv. over-expressing γ-tocopherol methyltransferase (γ-tmt) gene.

PubMed

Ghimire, Bimal Kumar; Son, Na-Young; Kim, Seung-Hyun; Yu, Chang Yeon; Chung, Ill-Min

2017-07-01

The effect of water stress and herbicide treatment on the phenolic compound concentration and photosynthesis rate in transgenic Codonopsis lanceolata plants over-expressing the γ-tmt gene was investigated and compared to that in control non-transgenic C. lanceolata plants. The total phenolic compound content was investigated using high-performance liquid chromatography combined with diode array detection in C. lanceolata seedlings 3 weeks after water stress and treatment with glyphosate. Changes in the composition of phenolic compounds were observed in leaf and root extracts from transformed C. lanceolata plants following water stress and treatment with glyphosate. The total concentration of phenolic compounds in the leaf extracts of transgenic samples after water stress ranged from 3455.13 ± 40.48 to 8695.00 ± 45.44 µg g -1 dry weight (DW), whereas the total concentration phenolic compound in the leaf extracts of non-transgenic control samples was 5630.83 ± 45.91 µg g -1  DW. The predominant phenolic compounds that increased after the water stress in the transgenic leaf were (+) catechin, benzoic acid, chlorogenic acid, ferulic acid, gallic acid, rutin, vanillic acid, and veratric acid. The total concentration of phenolic compounds in the leaf extracts of transgenic samples after glyphosate treatment ranged from 4744.37 ± 81.81 to 12,051.02 ± 75.00 µg g -1 DW, whereas the total concentration of the leaf extracts of non-transgenic control samples after glyphosate treatment was 3778.28 ± 59.73 µg g -1 DW. Major phenolic compounds that increased in the transgenic C. lanceolata plants after glyphosate treatment included kaempherol, gallic acid, myricetin, p-hydroxybenzjoic acid, quercetin, salicylic acid, t-cinnamic acid, catechin, benzoicacid, ferulic acid, protocatechuic acid, veratric acid, and vanillic acid. Among these, vanillic acid showed the greatest increase in both leaf and root extracts from transgenic plants relative to those from control C. lanceolata plants following treatment with glyphosate, which could affect the 5-enol-pyruvyl shikimate-3-phosphate (EPSP) synthase, an enzyme in the shikimate pathway. We observed enhanced stomatal conductance (gs) and photosynthesis rate (A) in the transgenic plants treated with water stress and glyphosate treatment. The results of this study demonstrated large variations in the functioning of secondary metabolites pathway in response glyphosate and water stress in transgenic C. lanceolata.

Phenolics and essential mineral profile of organic acid pretreated unripe banana flour.

PubMed

Anyasi, Tonna A; Jideani, Afam I O; Mchau, Godwin R A

2018-02-01

Banana fruit (Musa spp) though rich in essential minerals, has also been implicated for the presence of phytochemicals which nonetheless beneficial, can also act as mineral inhibitors when in forms such as phenolic compounds, phytates and tannins. This study assayed the essential macro and trace minerals as well as phenolic compounds present in unripe banana flour (UBF) obtained from the pulp of four different cultivars. Unripe banana flour was processed by oven drying in a forced air oven dryer at 70°C upon pretreatment with ascorbic, citric and lactic acid. Organic acid pretreatment was done separately on each unripe banana cultivar at concentrations of 10, 15 and 20g/L. Phenolic compounds were profiled using liquid chromatography mass spectrometry electrospray ion (LC-MS-ESI) while essential minerals were determined using inductively coupled plasma atomic emission spectroscopy (ICP-AES) and mass spectroscopy (ICP-MS) respectively. Results of LC-MS-ESI assay of phenolics revealed the presence of flavonoids: epicatechin and myricetin 3-O-rhamnosyl-glucoside in varying concentrations in UBF. Essential mineral profile indicated that Zinc had the least occurrence of 3.55mg/kg (p<0.05), while potassium was the most abundant mineral at 14746.73mg/kg in UBF of all four banana cultivars. Correlation between phenolic compounds and essential minerals using Pearson's Correlation Coefficient test revealed weak and inverse association between flavonoids and most macro and trace minerals present in UBF samples. Organic acid pretreatment thus exhibited little effect on phenolics and essential minerals of UBF samples, though, inhibitory influence of phenolic compounds was recorded on essential minerals. Copyright © 2017 The Authors. Published by Elsevier Ltd.. All rights reserved.

Cytoprotective effect of palm kernel cake phenolics against aflatoxin B1-induced cell damage and its underlying mechanism of action.

PubMed

Oskoueian, Ehsan; Abdullah, Norhani; Zulkifli, Idrus; Ebrahimi, Mahdi; Karimi, Ehsan; Goh, Yong Meng; Oskoueian, Armin; Shakeri, Majid

2015-10-30

Palm kernel cake (PKC), a by-product of the palm oil industry is abundantly available in many tropical and subtropical countries. The product is known to contain high levels of phenolic compounds that may impede the deleterious effects of fungal mycotoxins. This study focused on the evaluation of PKC phenolics as a potential cytoprotective agent towards aflatoxin B1 (AFB1)-induced cell damage. The phenolic compounds of PKC were obtained by solvent extraction and the product rich in phenolic compounds was labeled as phenolic-enriched fraction (PEF). This fraction was evaluated for its phenolic compounds composition. The antioxidant activity of PEF was determined by using 1,1-diphenyl-2-picryl-hydrazil scavenging activity, ferric reducing antioxidant power, inhibition of ß-carotene bleaching, and thiobarbituric acid reactive substances assays. The cytotoxicity assay and molecular biomarkers analyses were performed to evaluate the cytoprotective effects of PEF towards aflatoxin B1 (AFB1)-induced cell damage. The results showed that PEF contained gallic acid, pyrogallol, vanillic acid, caffeic acid, syringic acid, epicatechin, catechin and ferulic acid. The PEF exhibited free radical scavenging activity, ferric reducing antioxidant power, ß-carotene bleaching inhibition and thiobarbituric acid reactive substances inhibition. The PEF demonstrated cytoprotective effects in AFB1-treated chicken hepatocytes by reducing the cellular lipid peroxidation and enhancing antioxidant enzymes production. The viability of AFB1-treated hepatocytes was improved by PEF through up-regulation of oxidative stress tolerance genes and down-regulation of pro-inflammatory and apoptosis associated genes. The present findings supported the proposition that the phenolic compounds present in PKC could be a potential cytoprotective agent towards AFB1 cytotoxicity.

Polyphenolic compounds in date fruit seed (Phoenix dactylifera): characterisation and quantification by using UPLC-DAD-ESI-MS.

PubMed

Habib, Hosam M; Platat, Carine; Meudec, Emmanuelle; Cheynier, Veronique; Ibrahim, Wissam H

2014-04-01

Date fruit seeds have been demonstrated to possess high antioxidant activities due to their high content of flavonoids and phenolic compounds. The objective of this work was to identify and quantify the phenolic composition of date seeds. Two UPLC-DAD-ESI-MS analyses were performed on the seed of the Khalas variety as follows: (1) an analysis of simple phenolic compounds [phenolic acids, hydroxycinnamic acids, flavonols, flavones, flavan-3-ols (monomers, dimers and trimers)]; and (2) an analysis of all flavan-3-ols (monomers, and proanthocyanidin oligomers and polymers) after depolymerisation. The amount of total phenolic compounds before depolymerisation was found to be 2.194 ± 0.040 g kg(-1) date seed. The analysis of flavan-3-ol monomers and constitutive units of proanthocyanidins after depolymerisation revealed 50.180 ± 1.360 g kg(-1) flavan-3-ols with 46.800 ± 1.012 g kg(-1) epicatechin and 3.380 ± 0.349 g kg(-1) catechin. The results indicate that date seeds are a very rich source of bioactive compounds, thus constituting strong candidates for functional food additives and nutraceuticals. © 2013 Society of Chemical Industry.

Experimental design for extraction and quantification of phenolic compounds and organic acids in white "Vinho Verde" grapes.

PubMed

Dopico-García, M S; Valentão, P; Guerra, L; Andrade, P B; Seabra, R M

2007-01-30

An experimental design was applied for the optimization of extraction and clean-up processes of phenolic compounds and organic acids from white "Vinho Verde" grapes. The developed analytical method consisted in two steps: first a solid-liquid extraction of both phenolic compounds and organic acids and then a clean-up step using solid-phase extraction (SPE). Afterwards, phenolic compounds and organic acids were determined by high-performance liquid chromatography (HPLC) coupled to a diode array detector (DAD) and HPLC-UV, respectively. Plackett-Burman design was carried out to select the significant experimental parameters affecting both the extraction and the clean-up steps. The identified and quantified phenolic compounds were: quercetin-3-O-glucoside, quercetin-3-O-rutinoside, kaempferol-3-O-rutinoside, isorhamnetin-3-O-glucoside, quercetin, kaempferol and epicatechin. The determined organic acids were oxalic, citric, tartaric, malic, shikimic and fumaric acids. The obtained results showed that the most important variables were the temperature (40 degrees C) and the solvent (acid water at pH 2 with 5% methanol) for the extraction step and the type of sorbent (C18 non end-capped) for the clean-up step.

Preparation and use of maize tassels' activated carbon for the adsorption of phenolic compounds in environmental waste water samples.

PubMed

Olorundare, O F; Msagati, T A M; Krause, R W M; Okonkwo, J O; Mamba, B B

2015-04-01

The determination and remediation of three phenolic compounds bisphenol A (BPA), ortho-nitrophenol (o-NTP), parachlorophenol (PCP) in wastewater is reported. The analysis of these molecules in wastewater was done using gas chromatography (GC) × GC time-of-flight mass spectrometry while activated carbon derived from maize tassel was used as an adsorbent. During the experimental procedures, the effect of various parameters such as initial concentration, pH of sample solution, eluent volume, and sample volume on the removal efficiency with respect to the three phenolic compounds was studied. The results showed that maize tassel produced activated carbon (MTAC) cartridge packed solid-phase extraction (SPE) system was able to remove the phenolic compounds effectively (90.84-98.49%, 80.75-97.11%, and 78.27-97.08% for BPA, o-NTP, and PCP, respectively). The MTAC cartridge packed SPE sorbent performance was compared to commercially produced C18 SPE cartridges and found to be comparable. All the parameters investigated were found to have a notable influence on the adsorption efficiency of the phenolic compounds from wastewaters at different magnitudes.

Mechanisms of action of phenolic compounds in olive.

PubMed

Rafehi, Haloom; Ververis, Katherine; Karagiannis, Tom C

2012-06-01

Olive oil, an oil rich in monounsaturated fatty acids (MUFCs) and minor constituents including phenolic compounds, is a major component of the Mediterranean diet. The potential health benefits of the Mediterranean diet were highlighted by the seminal Seven Countries Study, and more contemporary research has identified olive oil as a major element responsible for these effects. It is emerging that the phenolic compounds are the most likely candidates accounting for the cardioprotective and cancer preventative effects of extra virgin olive oil (EVOO). In particular, the phenolic compound, hydroxytyrosol has been identified as one of the most potent antioxidants found in olive oil. This review will briefly consider historical aspects of olive oil research and the biological properties of phenolic compounds in olive oil will be discussed. The focus of the discussion will be related to the mechanisms of action of hydroxytyrosol. Studies have demonstrated that hydroxytyrosol induces apoptosis and cell cycle arrest in cancer cells. Further, research has shown that hydroxytyrosol can prevent cardiovascular disease by reducing the expression of adhesion molecules on endothelial cells and preventing the oxidation of low-density lipoprotein (LDL). The molecular mechanisms accounting for these effects are reviewed.

Phenolic compounds containing/neutral fractions extract and products derived therefrom from fractionated fast-pyrolysis oils

DOEpatents

Chum, Helena L.; Black, Stuart K.; Diebold, James P.; Kreibich, Roland E.

1993-01-01

A process for preparing phenol-formaldehyde novolak resins and molding compositions in which portions of the phenol normally contained in said resins are replaced by a phenol/neutral fractions extract obtained from fractionating fast-pyrolysis oils. The fractionation consists of a neutralization stage which can be carried out with aqueous solutions of bases or appropriate bases in the dry state, followed by solvent extraction with an organic solvent having at least a moderate solubility parameter and good hydrogen bonding capacity. Phenolic compounds-containing/neutral fractions extracts obtained by fractionating fast-pyrolysis oils from a lignocellulosic material, is such that the oil is initially in the pH range of 2-4, being neutralized with an aqueous bicarbonate base, and extracted into a solvent having a solubility parameter of approximately 8.4-9.11 [cal/cm.sup.3 ].sup.1/2 with polar components in the 1.8-3.0 range and hydrogen bonding components in the 2-4.8 range and the recovery of the product extract from the solvent with no further purification being needed for use in adhesives and molding compounds. The product extract is characterized as being a mixture of very different compounds having a wide variety of chemical functionalities, including phenolic, carbonyl, aldehyde, methoxyl, vinyl and hydroxyl. The use of the product extract on phenol-formaldehyde thermosetting resins is shown to have advantages over the conventional phenol-formaldehyde resins.

Extra-Virgin Olive Oil with Natural Phenolic Content Exerts an Anti-Inflammatory Effect in Adipose Tissue and Attenuates the Severity of Atherosclerotic Lesions in Ldlr-/-.Leiden Mice.

PubMed

Luque-Sierra, Amparo; Alvarez-Amor, Leticia; Kleemann, Robert; Martín, Franz; Varela, Lourdes M

2018-05-15

The present study investigates the effect of olive oils with different phenolic content in high-fat diets (HFDs) on hypertrophy and inflammation in adipose tissue and associated atherosclerosis, in the context of obesity. Ldlr-/-.Leiden mice were fed three different HFDs for 32 weeks and were compared with mice fed the standard low-fat diet (LFD). The different fats provided in the HFDs were lard (HFD-L), extra-virgin olive oil (EVOO; 79 mg kg -1 of phenolic compounds, HFD-EVOO), or EVOO rich in phenolic compounds (OL, 444 mg kg -1 of phenolic compounds, HFD-OL). All HFD-fed mice became obese, but only HFD-L-induced adipocyte hypertrophy. HFD-EVOO mice exhibited the greatest levels of Adiponectin in adipose tissue and presented atherosclerotic lesions similar to the LFD group, with a very low count of monocyte/macrophage compared with HFD-L and HFD-OL mice. Enrichment of the phenolic content of olive oil reduced the secretion of nitrites/nitrates in the aorta, but atherosclerosis was not attenuated in HFD-OL mice compared to other HFD mice. Consumption of olive oil with a natural content of phenolic compounds attenuates adipose tissue hypertrophy and inflammation and exerts antiatherosclerotic effects in mice. A higher phenolic content of olive oil did not provide further benefits in the prevention of atherosclerosis. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Identification and Phytotoxicity Assessment of Phenolic Compounds in Chrysanthemoides monilifera subsp. monilifera (Boneseed).

PubMed

Al Harun, Md Abdullah Yousuf; Johnson, Joshua; Uddin, Md Nazim; Robinson, Randall W

2015-01-01

Chrysanthemoides monilifera subsp. monilifera (boneseed), a weed of national significance in Australia, threatens indigenous species and crop production through allelopathy. We aimed to identify phenolic compounds produced by boneseed and to assess their phytotoxicity on native species. Phenolic compounds in water and methanol extracts, and in decomposed litter-mediated soil leachate were identified using HPLC, and phytotoxicity of identified phenolics was assessed (repeatedly) through a standard germination bioassay on native Isotoma axillaris. The impact of boneseed litter on native Xerochrysum bracteatum was evaluated using field soil in a greenhouse. Collectively, we found the highest quantity of phenolic compounds in boneseed litter followed by leaf, root and stem. Quantity varied with extraction media. The rank of phenolics concentration in boneseed was in the order of ferulic acid > phloridzin > catechin > p-coumaric acid and they inhibited germination of I. axillaris with the rank of ferulic acid > catechin > phloridzin > p-coumaric acid. Synergistic effects were more severe compared to individual phenolics. The litter-mediated soil leachate (collected after15 days) exhibited strong phytotoxicity to I. axillaris despite the level of phenolic compounds in the decomposed leachate being decreased significantly compared with their initial level. This suggests the presence of other unidentified allelochemicals that individually or synergistically contributed to the phytotoxicity. Further, the dose response phytotoxic impacts exhibited by the boneseed litter-mediated soil to native X. bracteatum in a more naturalistic greenhouse experiment might ensure the potential allelopathy of other chemical compounds in the boneseed invasion. The reduction of leaf relative water content and chlorophyll level in X. bracteatum suggest possible mechanisms underpinning plant growth inhibition caused by boneseed litter allelopathy. The presence of a substantial quantity of free proline in the target species also suggests that the plant was in a stressed condition due to litter allelopathy. These findings are important for better understanding the invasive potential of boneseed and in devising control strategies.

Identification and Phytotoxicity Assessment of Phenolic Compounds in Chrysanthemoides monilifera subsp. monilifera (Boneseed)

PubMed Central

Al Harun, Md Abdullah Yousuf; Johnson, Joshua; Uddin, Md Nazim; Robinson, Randall W.

2015-01-01

Chrysanthemoides monilifera subsp. monilifera (boneseed), a weed of national significance in Australia, threatens indigenous species and crop production through allelopathy. We aimed to identify phenolic compounds produced by boneseed and to assess their phytotoxicity on native species. Phenolic compounds in water and methanol extracts, and in decomposed litter-mediated soil leachate were identified using HPLC, and phytotoxicity of identified phenolics was assessed (repeatedly) through a standard germination bioassay on native Isotoma axillaris. The impact of boneseed litter on native Xerochrysum bracteatum was evaluated using field soil in a greenhouse. Collectively, we found the highest quantity of phenolic compounds in boneseed litter followed by leaf, root and stem. Quantity varied with extraction media. The rank of phenolics concentration in boneseed was in the order of ferulic acid > phloridzin > catechin > p-coumaric acid and they inhibited germination of I. axillaris with the rank of ferulic acid > catechin > phloridzin > p-coumaric acid. Synergistic effects were more severe compared to individual phenolics. The litter-mediated soil leachate (collected after15 days) exhibited strong phytotoxicity to I. axillaris despite the level of phenolic compounds in the decomposed leachate being decreased significantly compared with their initial level. This suggests the presence of other unidentified allelochemicals that individually or synergistically contributed to the phytotoxicity. Further, the dose response phytotoxic impacts exhibited by the boneseed litter-mediated soil to native X. bracteatum in a more naturalistic greenhouse experiment might ensure the potential allelopathy of other chemical compounds in the boneseed invasion. The reduction of leaf relative water content and chlorophyll level in X. bracteatum suggest possible mechanisms underpinning plant growth inhibition caused by boneseed litter allelopathy. The presence of a substantial quantity of free proline in the target species also suggests that the plant was in a stressed condition due to litter allelopathy. These findings are important for better understanding the invasive potential of boneseed and in devising control strategies. PMID:26465595

A Review of Molecular Mechanisms of the Anti-Leukemic Effects of Phenolic Compounds in Honey

PubMed Central

Abubakar, Murtala B.; Abdullah, Wan Zaidah; Sulaiman, Siti Amrah; Suen, Ang Boon

2012-01-01

Hematologic malignancies constitute about 9% of all new cases of cancers as reported via the GLOBOCAN series by International Agency for Research on Cancer (IARC) in 2008. So far, the conventional therapeutic and surgical approaches to cancer therapy have not been able to curtail the rising incidence of cancers, including hematological malignancies, worldwide. The last decade has witnessed great research interest in biological activities of phenolic compounds that include anticancer, anti-oxidation and anti-inflammation, among other things. A large number of anticancer agents combat cancer through cell cycle arrest, induction of apoptosis and differentiation, as well as through inhibition of cell growth and proliferation, or a combination of two or more of these mechanisms. Various phenolic compounds from different sources have been reported to be promising anticancer agents by acting through one of these mechanisms. Honey, which has a long history of human consumption both for medicinal and nutritional uses, contains a variety of phenolic compounds such as flavonoids, phenolic acids, coumarins and tannins. This paper presents a review on the molecular mechanisms of the anti-leukemic activity of various phenolic compounds on cell cycle, cell growth and proliferation and apoptosis, and it advocates that more studies should be conducted to determine the potential role of honey in both chemoprevention and chemotherapy in leukemia. PMID:23203111

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

PubMed Central

de Araújo, Keline Medeiros; de Lima, Alessandro; Silva, Jurandy do N.; Rodrigues, Larissa L.; Amorim, Adriany G. N.; Quelemes, Patrick V.; dos Santos, Raimunda C.; Rocha, Jefferson A.; de Andrades, Éryka O.; Leite, José Roberto S. A.; Mancini-Filho, Jorge; da Trindade, Reginaldo Almeida

2014-01-01

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. PMID:26784670

Synthesis and antioxidant activity of star-shape phenolic antioxidants catalyzed by acidic nanocatalyst based on reduced graphene oxide.

PubMed

Golestanzadeh, Mohsen; Naeimi, Hossein; Zahraie, Zohreh

2017-02-01

Phenolic antioxidants play important role in prevention of oxidation in different industrials. The research objective in the current study was synthesis and evaluate of antioxidant activity of star-shape phenolic antioxidants. The synthetic compounds were prepared in the presence of sulfonated reduced graphene oxide. The antioxidant activity of synthesized compounds was investigated by spectrophotometrically method according to the DPPH assay. Overall, these compounds are potentially important antioxidant and also to limit activity of reactive oxygen species. Copyright © 2016 Elsevier B.V. All rights reserved.

Stability of bioactive compounds in butiá (Butia odorata) fruit pulp and nectar.

PubMed

Hoffmann, Jessica Fernanda; Zandoná, Giovana Paula; Dos Santos, Priscila Silveira; Dallmann, Camila Müller; Madruga, Francine Bonemann; Rombaldi, Cesar Valmor; Chaves, Fábio Clasen

2017-12-15

Butia odorata is a palm tree native to southern Brazil whose fruit (known as butiá) and leaves are used to make many food products and crafts. Butiá contain several biologically active compounds with potential health benefits. However, processing conditions can alter quality attributes including bioactive compound content. This study evaluated the stability of bioactive compounds in butiá pulp upon pasteurization, during 12months of frozen storage, and in butiá nectar after a 3-month storage period. Pulp pasteurization resulted in a reduction in phenolic, flavonoid, carotenoid, and ascorbic acid contents. After a 12-month frozen storage period, flavonoid, phenolic, and ascorbic acid contents decreased while carotenoid content remained unaltered. Carotenoid, ascorbic acid, and phenolic contents were unaffected by the 3-month storage of butiá nectar; however, flavonoid content and antioxidant potential were reduced. Despite bioactive compound degradation upon heat treatment and storage, butiá nectar remained rich in phenolics, especially (-)-epicatechin, rutin, and (+)-catechin. Copyright © 2017 Elsevier Ltd. All rights reserved.

Identification of phenolic compounds by liquid chromatography-mass spectrometry in seventeen species of wild mushrooms in Central Mexico and determination of their antioxidant activity and bioactive compounds.

PubMed

Yahia, Elhadi M; Gutiérrez-Orozco, Fabiola; Moreno-Pérez, Marco A

2017-07-01

Wild mushrooms are important for the diet of some communities in Mexico. However, limited information exists on their chemical composition, contribution to the diet, and health effects. We characterized seventeen wild mushroom species growing in the state of Queretaro in Central Mexico. Most species analyzed were edible, but also included nonedible, medicinal, poisonous and toxic specimens. Whole mushrooms (caps and stipes) were characterized for water content, color, and total content of phenolic compounds, flavonoids and anthocyanins. In vitro antioxidant capacity was measured by FRAP and DPPH assays. Phenolic compounds were identified and quantified by HPLC-mass spectrometry. All species analyzed were found to possess antioxidant activity in vitro and a wide range of phenolic and organic compounds were identified. Our results add to the limited information available on the composition and potential nutritional and health value of wild mushrooms. Further analyses of their bioactivities are warranted. Copyright © 2017 Elsevier Ltd. All rights reserved.

RP-HPTLC densitometric determination and validation of vanillin and related phenolic compounds in accelerated solvent extract of Vanilla planifolia*.

PubMed

Sharma, Upendra Kumar; Sharma, Nandini; Gupta, Ajai Prakash; Kumar, Vinod; Sinha, Arun Kumar

2007-12-01

A simple, fast and sensitive RP-HPTLC method is developed for simultaneous quantitative determination of vanillin and related phenolic compounds in ethanolic extracts of Vanilla planifolia pods. In addition to this, the applicability of accelerated solvent extraction (ASE) as an alternative to microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE) and Soxhlet extraction was also explored for the rapid extraction of phenolic compounds in vanilla pods. Good separation was achieved on aluminium plates precoated with silica gel RP-18 F(254S) in the mobile phase of methanol/water/isopropanol/acetic acid (30:65:2:3, by volume). The method showed good linearity, high precision and good recovery of compounds of interest. ASE showed good extraction efficiency in less time as compared to other techniques for all the phenolic compounds. The present method would be useful for analytical research and for routine analysis of vanilla extracts for their quality control.

Inhibitory Effect of Furanic and Phenolic Compounds on Exoelectrogenesis in a Microbial Electrolysis Cell Bioanode

DOE PAGES

Zeng, Xiaofei; Borole, Abhijeet P.; Pavlostathis, Spyros G.

2016-09-09

Furanic and phenolic compounds are 20 lignocellulose-derived compounds known to inhibit to H2- and ethanol- producing microorganisms in dark fermentation. Bioelectrochemical conversion of furanic and phenolic compounds to electricity or H2 has recently been demonstrated as a productive method to use these compounds. However, potential inhibitory effect of furanic and phenolic compounds on exoelectrogenesis in bioelectrochemical systems is not well understood. This study systematically investigated the inhibitory effect of furfural (FF), 5-hydroxymethylfurfural (HMF), syringic acid (SA), vanillic acid (VA), and 4-hydroxybenzoic acid (HBA) on exoelectrogenesis in the bioanode of a microbial electrolysis cell. A mixture of these five compounds atmore » an increasing initial total concentration from 0.8 to 8.0 g/L resulted in current decrease up to 91%. The observed inhibition primarily affected exoelectrogenesis, instead of non-exoelectrogenic biotransformation pathways (e.g., fermentation) of the five compounds. Furthermore, the parent compounds at a high concentration, as opposed to their biotransformation products, were responsible for the observed inhibition. Tests with individual compounds show that all five parent compounds contributed to the observed inhibition by the mixture. The IC50 (concentration resulting in 50% current decrease) was estimated as 2.7 g/L for FF, 3.0 g/L for HMF, 1.9 g/L for SA, 2.1 g/L for VA and 2.0 g/L for HBA. Nevertheless, these compounds below their non-inhibitory concentrations jointly resulted in significant inhibition as a mixture. Catechol and phenol, which were persistent biotransformation products of the mixture, inhibited exoelectrogens at high concentrations, but to a lesser extent than the parent compounds. Recovery of exoelectrogenesis from inhibition by all compounds was observed, except for catechol, which resulted in irreversible inhibition. The reversibility of inhibition, as well as the observed difference in recovery rates, suggest different modes of exoelectrogenesis inhibition, related to the hydrophobicity of the inhibiting compounds.« less

A novel antibacterial and antifungal phenolic compound from the endophytic fungus Pestalotiopsis mangiferae.

PubMed

Subban, Kamalraj; Subramani, Ramesh; Johnpaul, Muthumary

2013-01-01

A novel phenolic compound, 4-(2,4,7-trioxa-bicyclo[4.1.0]heptan-3-yl) phenol (1), was isolated from Pestalotiopsis mangiferae, an endophytic fungus associated with Mangifera indica Linn. The structure of the compound was elucidated on the basis of comprehensive spectral analysis (UV, IR, ¹H-, ¹³C- and 2D-NMR, as well as HRESI-MS). Compound (1) shows potent antibacterial and antifungal activity against Bacillus subtilis, Klebsiella pneumoniae, Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa and Candida albicans. The transmission electron microscope study for the mode of inhibition of compound (1) on bacterial pathogens revealed the destruction of bacterial cells by cytoplasm agglutination with the formation of pores in cell wall membranes.

RESPONSE OF PHENOLIC METABOLISM INDUCED BY ALUMINIUM TOXICITY IN FAGOPYRUM ESCULENTUM MOENCH. PLANTS.

PubMed

Smirnov, O E; Kosyan, A M; Kosyk, O I; Taran, N Yu

2015-01-01

Buckwheat genus (Fagopyrum Mill.) is one of the aluminium tolerant taxonomic units of plants. The aim of the study was an evaluation of the aluminium (50 μM effect on phenolic accumulation in various parts of buckwheat plants (Fagopyrum esculentum Moench). Detection of increasing of total phenolic content, changes in flavonoid and anthocyanin content and phenylalanine ammonia-lyase activity (PAL) were revealed over a period of 10 days of exposure to aluminium. The most significant effects of aluminium treatment on phenolic compounds accumulation were total phenolic content increasing (by 27.2%) and PAL activity rising by 2.5 times observed in leaves tissues. Received data could be helpful to understand the aluminium tolerance principles and relationships of phenolic compounds to aluminium phytotoxicity.

Altered transport and metabolism of phenolic compounds in obesity and diabetes: implications for functional food development and assessment

USDA-ARS?s Scientific Manuscript database

Interest in application of phenolic compounds from diet or supplements for prevention of chronic diseases has grown significantly, but efficacy of such approaches in humans is largely dependent on the bioavailability and metabolism of these compounds. While food and dietary factors have been the foc...

A new phenolic glycoside from the stem of Dendrobium nobile.

PubMed

Zhou, Xue-Ming; Zheng, Cai-Juan; Wu, Jia-Ting; Chen, Guang-Ying; Zhang, Bin; Sun, Chong-Ge

2017-05-01

A new phenolic glycoside dendroside (1), together with seven known compounds (2-8) were isolated from the stems of Dendrobium nobile. The structures of these compounds were elucidated using comprehensive spectroscopic methods. The inhibitory activities of all compounds against three cancer cell lines HeLa, MCF-7 and A549 were evaluated.

Recovery of natural antioxidants from spent coffee grounds.

PubMed

Panusa, Alessia; Zuorro, Antonio; Lavecchia, Roberto; Marrosu, Giancarlo; Petrucci, Rita

2013-05-01

Spent coffee grounds (SCG) were extracted with an environmentally friendly procedure and analyzed to evaluate the recovery of relevant natural antioxidants for use as nutritional supplements, foods, or cosmetic additives. SCG were characterized in terms of their total phenolic content by the Folin-Ciocalteu procedure and antioxidant activity by the DPPH scavenging assay. Flavonoid content was also determined by a colorimetric assay. The total phenolic content was strongly correlated with the DPPH scavenging activity, suggesting that phenolic compounds are mainly responsible for the antioxidant activity of SCG. An UHPLC-PDA-TOF-MS system was used to separate, identify, and quantify phenolic and nonphenolic compounds in the SCG extracts. Important amounts of chlorogenic acids (CGA) and related compounds as well as caffeine (CAF) evidenced the high potential of SCG, a waste material that is widely available in the world, as a source of natural phenolic antioxidants.

Phenolic acids, hydrolyzable tannins, and antioxidant activity of geopropolis from the stingless bee Melipona fasciculata Smith.

PubMed

Dutra, Richard Pereira; Abreu, Bruno Vinicius de Barros; Cunha, Mayara Soares; Batista, Marisa Cristina Aranha; Torres, Luce Maria Brandão; Nascimento, Flavia Raquel Fernandes; Ribeiro, Maria Nilce Sousa; Guerra, Rosane Nassar Meireles

2014-03-26

Geopropolis is a mixture of plant resins, waxes, and soil produced by the stingless bee Melipona fasciculata Smith. This paper describes the antioxidant activity and chemical composition of geopropolis produced by M. fasciculata. The total phenolic content determined with the Folin-Ciocalteu reagent was highest in the ethyl acetate fraction and hydroalcoholic extract. Antioxidant activity was assayed by the in vitro DPPH, ABTS, and FRAP assays. The hydroalcoholic extract and fractions of geopropolis, except for the hexane fraction, exhibited antioxidant activity against DPPH, ABTS, and FRAP. The phenolic compounds were identified by HPLC-DAD-MS on the basis of the evaluation of their UV-vis absorption maxima (λmax) and mass spectral analysis. Eleven compounds belonging to the classes of phenolic acids and hydrolyzable tannins (gallotannins and ellagitannins) were tentatively identified. These compounds are responsible for the antioxidant activity and high phenolic content of geopropolis produced by M. fasciculata.

Transglycosylation reactions, a main mechanism of phenolics incorporation in coffee melanoidins: Inhibition by Maillard reaction.

PubMed

Moreira, Ana S P; Nunes, Fernando M; Simões, Cristiana; Maciel, Elisabete; Domingues, Pedro; Domingues, M Rosário M; Coimbra, Manuel A

2017-07-15

Under roasting conditions, polysaccharides depolymerize and also are able to polymerize, forming new polymers through non-enzymatic transglycosylation reactions (TGRs). TGRs can also occur between carbohydrates and aglycones, such as the phenolic compounds present in daily consumed foods like coffee. In this study, glycosidically-linked phenolic compounds were quantified in coffee melanoidins, the polymeric nitrogenous brown-colored compounds formed during roasting, defined as end-products of Maillard reaction. One third of the phenolics present were in glycosidically-linked form. In addition, the roasting of solid-state mixtures mimicking coffee beans composition allowed the conclusion that proteins play a regulatory role in TGRs extension and, consequently, modulate melanoidins composition. Overall, the results obtained showed that TGRs are a main mechanism of phenolics incorporation in melanoidins and are inhibited by amino groups through Maillard reaction. Copyright © 2017 Elsevier Ltd. All rights reserved.

Mapping the genetic and tissular diversity of 64 phenolic compounds in Citrus species using a UPLC–MS approach

PubMed Central

Durand-Hulak, Marie; Dugrand, Audray; Duval, Thibault; Bidel, Luc P. R.; Jay-Allemand, Christian; Froelicher, Yann; Bourgaud, Frédéric; Fanciullino, Anne-Laure

2015-01-01

Background and Aims Phenolic compounds contribute to food quality and have potential health benefits. Consequently, they are an important target of selection for Citrus species. Numerous studies on this subject have revealed new molecules, potential biosynthetic pathways and linkage between species. Although polyphenol profiles are correlated with gene expression, which is responsive to developmental and environmental cues, these factors are not monitored in most studies. A better understanding of the biosynthetic pathway and its regulation requires more information about environmental conditions, tissue specificity and connections between competing sub-pathways. This study proposes a rapid method, from sampling to analysis, that allows the quantitation of multiclass phenolic compounds across contrasting tissues and cultivars. Methods Leaves and fruits of 11 cultivated citrus of commercial interest were collected from adult trees grown in an experimental orchard. Sixty-four phenolic compounds were simultaneously quantified by ultra-high-performance liquid chromatography coupled with mass spectrometry. Key Results Combining data from vegetative tissues with data from fruit tissues improved cultivar classification based on polyphenols. The analysis of metabolite distribution highlighted the massive accumulation of specific phenolic compounds in leaves and the external part of the fruit pericarp, which reflects their involvement in plant defence. The overview of the biosynthetic pathway obtained confirmed some regulatory steps, for example those catalysed by rhamnosyltransferases. The results suggest that three other steps are responsible for the different metabolite profiles in ‘Clementine’ and ‘Star Ruby’ grapefruit. Conclusions The method described provides a high-throughput method to study the distribution of phenolic compounds across contrasting tissues and cultivars in Citrus, and offers the opportunity to investigate their regulation and physiological roles. The method was validated in four different tissues and allowed the identification and quantitation of 64 phenolic compounds in 20 min, which represents an improvement over existing methods of analysing multiclass polyphenols. PMID:25757470

The Extent of Fermentative Transformation of Phenolic Compounds in the Bioanode Controls Exoelectrogenic Activity in a Microbial Electrolysis Cell

DOE PAGES

Zeng, Xiaofei; Collins, Maya; Borole, Abhijeet P.; ...

2016-11-27

Phenolic compounds in hydrolysate/pyrolysate and wastewater streams produced during the pretreatment of lignocellulosic biomass for biofuel production present a significant challenge in downstream processes. Bioelectrochemical systems are increasingly recognized as an alternative technology to handle biomass-derived streams and to promote water reuse in biofuel production. Thus, a thorough understanding of the fate of phenolic compounds in bioanodes is urgently needed. The present study investigated the biotransformation of three structurally similar phenolic compounds (syringic acid, SA; vanillic acid, VA; 4-hydroxybenzoic acid, HBA), and their individual contribution to exoelectrogenesis in a microbial electrolysis cell (MEC) bioanode. Fermentation of SA resulted in themore » highest exoelectrogenic activity among the three compounds tested, with 50% of the electron equivalents converted to current, compared to 12 and 9% for VA and HBA, respectively. The biotransformation of SA, VA and HBA was initiated by demethylation and decarboxylation reactions common to all three compounds, resulting in their corresponding hydroxylated analogs. SA was transformed to pyrogallol (1,2,3-trihydroxybenzene), whose aromatic ring was then cleaved via a phloroglucinol pathway, resulting in acetate production, which was then used in exoelectrogenesis. In contrast, more than 80% of VA and HBA was converted to catechol (1,2-dihydroxybenzene) and phenol (hydroxybenzene) as their respective dead-end products. The persistence of catechol and phenol is explained by the fact that the phloroglucinol pathway does not apply to di- or mono-hydroxylated benzenes. Previously reported, alternative ring-cleaving pathways were either absent in the bioanode microbial community or unfavorable due to high energy-demand reactions. With the exception of acetate oxidation, all biotransformation steps in the bioanode occurred via fermentation, independently of exoelectrogenesis. Therefore, the observed exoelectrogenic activity in batch runs conducted with SA, VA and HBA was controlled by the extent of fermentative transformation of the three phenolic compounds in the bioanode, which is related to the number and position of the methoxy and hydroxyl substituents.« less

Phylogenetic and functional diversity of metagenomic libraries of phenol degrading sludge from petroleum refinery wastewater treatment system.

PubMed

Silva, Cynthia C; Hayden, Helen; Sawbridge, Tim; Mele, Pauline; Kruger, Ricardo H; Rodrigues, Marili Vn; Costa, Gustavo Gl; Vidal, Ramon O; Sousa, Maíra P; Torres, Ana Paula R; Santiago, Vânia Mj; Oliveira, Valéria M

2012-03-27

In petrochemical refinery wastewater treatment plants (WWTP), different concentrations of pollutant compounds are received daily in the influent stream, including significant amounts of phenolic compounds, creating propitious conditions for the development of particular microorganisms that can rapidly adapt to such environment. In the present work, the microbial sludge from a refinery WWTP was enriched for phenol, cloned into fosmid vectors and pyrosequenced. The fosmid libraries yielded 13,200 clones and a comprehensive bioinformatic analysis of the sequence data set revealed a complex and diverse bacterial community in the phenol degrading sludge. The phylogenetic analyses using MEGAN in combination with RDP classifier showed a massive predominance of Proteobacteria, represented mostly by the genera Diaphorobacter, Pseudomonas, Thauera and Comamonas. The functional classification of phenol degrading sludge sequence data set generated by MG-RAST showed the wide metabolic diversity of the microbial sludge, with a high percentage of genes involved in the aerobic and anaerobic degradation of phenol and derivatives. In addition, genes related to the metabolism of many other organic and xenobiotic compounds, such as toluene, biphenyl, naphthalene and benzoate, were found. Results gathered herein demonstrated that the phenol degrading sludge has complex phylogenetic and functional diversities, showing the potential of such community to degrade several pollutant compounds. This microbiota is likely to represent a rich resource of versatile and unknown enzymes which may be exploited for biotechnological processes such as bioremediation.

Comparison on phenolic compounds and antioxidant properties of cabernet sauvignon and merlot wines from four wine grape-growing regions in China.

PubMed

Jiang, Bao; Zhang, Zhen-Wen

2012-07-25

The antioxidant activities in the Cabernet Sauvignon and Merlot wines from four wine grape-growing regions in China were measured by different analytical assays: 2,2-diphenyl-1-picrylhydrazyl (DPPH·), cupric reducing antioxidant capacity (CUPRAC), superoxide radical-scavenging activity (SRSA) and the contents of total phenols, total flavonoids, total flavanols and total anthocyanins were determined. The results showed that the contents of phenolic compounds and the levels of antioxidant activity in the wine samples greatly varied with cultivar and environmental factors of vine growth. The contents of phenolic compounds and antioxidant activities in Cabernet Sauvignon and Merlot wines from the Yuquanying region of Ningxia were significantly higher than other three regions, followed by the wines from Shacheng region of Hebei, and these parameters were the lowest in Cabernet Sauvignon and Merlot wines from the Changli regions of Hebei and Xiangning region of Shanxi. Taken together, a close relationship between phenolic subclasses and antioxidant activity was observed for the wine samples. Moreover, there were significant discrepancies in the individual phenolic composition and content of four regional Cabernet Sauvignon and Merlot wines, among which the individual phenolic compounds (catechin, epicatechin, cinnamic acid, quercetin-3-O-glucuronide, quercetin-3-O-glucoside, laricitrin-3-O-glucoside and isorhamnetin-3-O-glucoside) revealed a significant correlation (p < 0.05) with the antioxidant capacity in present study, especially for catechin and epicatechin.

Profiling and quantification of phenolic compounds in Camellia seed oils: Natural tea polyphenols in vegetable oil.

PubMed

Wang, Xiaoqin; Zeng, Qiumei; Del Mar Contreras, María; Wang, Lijuan

2017-12-01

In Asia, tea seed oils (seed oils from Camellia oleifera, C. chekiangoleosa, and C. sinensis) are used in edible, medicinal, and cosmetic applications. However, these oils differ in their fatty acid contents, and there is little known about their phenolic compounds. Here we analyzed the phenolic compounds of seed oils from three species gathered from 15 regions of China. Twenty-four phenolic compounds were characterized by HPLC-Q-TOF-MS, including benzoic acids (6), cinnamic acids (6), a hydroxyphenylacetic acid, flavanols (4), flavonols (3), flavones (2), and dihydroflavonoids (2). Some of these phenolic compounds had not previously been reported from C. sinensis (20), C. oleifera (15), and C. chekiangoleosa (24) seed oils. Quantification was done by HPLC-QqQ-MS using 24 chemical standards. The total concentrations in the studied samples ranged from 20.56 to 88.56μg/g. Phenolic acids were the most abundant class, accounting for 76.2-90.4%, with benzoic acid, found at up to 18.87μg/g. The concentration of catechins, typical of tea polyphenols, ranged between 2.1% and 9.7%, while the other flavonoids varied from 4.2% to 17.8%. Although the cultivation region affected the phenolic composition of the Camellia seed oils, in our hierarchical clustering analysis, the samples clustered according to species. The phenolic composition of the seed oils from C. oleifera and C. chekiangoelosa were similar. We found that the phenolic categories in Camellia seed oils were similar to tea polyphenols, thereby identifying a source of liposoluble tea polyphenols and potentially accounting for some of the reported activities of these oils. In addition, this work provides basic data that allows distinction of various Camellia seed oils, as well as improvements to be made in their quality standards. Copyright © 2017 Elsevier Ltd. All rights reserved.

Chemical composition and antioxidant activity of phenolic compounds and essential oils from Calamintha nepeta L.

PubMed

Khodja, Nabyla Khaled; Boulekbache, Lila; Chegdani, Fatima; Dahmani, Karima; Bennis, Faiza; Madani, Khodir

2018-05-24

Background Essential oils, infusion and decoction extracts of Calamintha nepeta L. were evaluated for their bioactive substances (polyphenols and essential oils) and antioxidant activities. Methods The amounts of phenolic compounds were determined by colorimetric assays and identified by high performance and liquid chromatography coupled with ultraviolet detector (HPLC-UV) method. The chemical composition of essential oils was determined by gas-chromatography coupled with mass spectrometry (GC/MS) method. For the evaluation of the antioxidant activity of essential oils and extracts, two different assays (reducing power and DPPH radical scavenging activity) were used. Results Infusion extract presented the highest phenolic content, followed by the decoction one, while the lowest amount was observed in essential oils. The amount of flavonoids of the decocted extract was higher than that of the infused one. The phenolic profile of C. nepeta infusion and decoction extracts revealed the presence of 28 and 13 peaks, respectively. Four phenolics compounds were identified in infusion (gallic acid (GA), rosmarinic acid (RA), caffeine (C) and caffeic acid (CA)) and two were identified in decoction (GA and RA). The chemical composition of essential oils revealed the presence of 29 compounds, accounting for the 99.7% of the total oils. Major compounds of essential oil (EO) were trans-menthone (50.06%) and pulegone (33.46%). Infusion and decoction extracts revealed an interesting antioxidant activity which correlates positively with their total phenolic contents. Conclusions These results showed that Calamintha nepeta could be considered as a valuable source of phenolics and essential oils with potent antioxidant activity.

Bioactive compounds, RP-HPLC analysis of phenolics, and antioxidant activity of some Portuguese shrub species extracts.

PubMed

Luís, Angelo; Domingues, Fernanda; Duarte, Ana Paula

2011-12-01

In the ecosystem of Serra Da Estrela, some plant species have the potential to be used as raw material for extraction of bioactive products. The goal of this work was to determine the phenolic, flavonoid, tannin and alkaloid contents of the methanolic extracts of some shrubs (Echinospartum ibericum, Pterospartum tridentatum, Juniperus communis, Ruscus aculeatus, Rubus ulmifolius, Hakea sericea, Cytisus multiflorus, Crataegus monogyna, Erica arborea and Ipomoea acuminata), and then to correlate the phenolic compounds and flavonoids with the antioxidant activity of each extract. The Folin-Ciocalteu's method was used for the determination of total phenols, and tannins were then precipitated with polyvinylpolypyrrolidone (PVPP); a colorimetric method with aluminum chloride was used for the determination of flavonoids, and a Dragendorff's reagent method was used for total alkaloid estimation. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) and beta-carotene bleaching tests were used to assess the antioxidant activity of extracts. The identification of phenolic compounds present in extracts was performed using RP-HPLC. A positive linear correlation between antioxidant activity index and total phenolic content of methanolic extracts was observed. The RP-HPLC procedure showed that the most common compounds were ferulic and ellagic acids and quercetin. Most of the studied shrubs have significant antioxidant properties that are probably due to the existence of phenolic compounds in the extracts. It is noteworthy to emphasize that for Echinospartum ibericum, Hakea sericea and Ipomoea acuminata, to the best of our knowledge, no phytochemical studies have been undertaken nor their use in traditional medicine been described.

The multifunctionality of berries toward blood platelets and the role of berry phenolics in cardiovascular disorders.

PubMed

Olas, Beata

2017-09-01

Diet and nutrition have an important influence on the prophylaxis and progression of cardiovascular disease; one example is the inhibition of blood platelet functions by specific components of fruits and vegetables. Garlic, onion, ginger, dark chocolate and polyunsaturated fatty acids all reduce blood platelet aggregation. A number of fruits contain a range of cardioprotective antioxidants and vitamins, together with a large number of non-nutrient phytochemicals such as phenolic compounds, which may possess both antioxidant properties and anti-platelet activity. Fresh berries and berry extracts possess high concentrations of phenolic compounds, i.e. phenolic acid, stilbenoids, flavonoids and lignans. The aim of this review article is to provide an overview of current knowledge of the anti-platelet activity of berries, which form an integral part of the human diet. It describes the effects of phenolic compounds present in a number of berries, i.e. black chokeberries - aronia berries (Aronia melanocarpa), blueberries (Vaccinium myrtillus), cranberries (Vaccinium sect. Oxycoccus), sea buckthorn berries (Hippophae rhamnoides) and grapes (Vitis), as well as various commercial products from berries (i.e. juices), on platelets and underlying mechanisms. Studies show that the effects of berries on platelet activity are dependent on not only the concentrations of the phenolic compounds in the berries or the class of phenolic compounds, but also the types of berry and the form (fresh berry, juice or medicinal product). Different results indicate that berries may play a role in the prevention of cardiovascular disorders, but the development of well-controlled clinical studies with berries is encouraged.

Effect of Microwave-Assisted Extraction on the Phenolic Compounds and Antioxidant Capacity of Blackthorn Flowers.

PubMed

Lovrić, Vanja; Putnik, Predrag; Kovačević, Danijela Bursać; Jukić, Marijana; Dragović-Uzelac, Verica

2017-06-01

This research was undertaken to investigate the influence of extraction parameters during microwave-assisted extraction on total phenolic content, total flavonoids, total hydroxycinnamic acids and total flavonols of blackthorn flowers as well as to evaluate the antioxidant capacity by two different methods (2,2-diphenyl-1-picrylhydrazyl free radical scavenging capacity and ferric reducing antioxidant power assays). The investigated extraction parameters were: solvent type and volume fraction of alcohol in solvent (50 and 70% aqueous solutions of ethanol and methanol), extraction time (5, 15 and 25 min) and extraction temperature (40, 50 and 60 °C) controlled by microwave power of 100, 200 and 300 W. Multivariate analysis of variance (MANOVA) was used to evaluate the differences at a 95% confidence level (p≤0.05). The obtained results show that aqueous solution of ethanol was more appropriate solvent for extraction of phenolic compounds (total flavonoids, total hydroxycinnamic acids and total flavonols) than aqueous solution of methanol. The amount of phenolic compounds was higher in 70% aqueous solution of ethanol or methanol, while higher antioxidant capacity was observed in 50% aqueous solution of methanol. Higher temperature of extraction improved the amount of phenolic compounds and also antioxidant capacity determined by 2,2-diphenyl-1-picrylhydrazyl free radical scavenging capacity assay. Extensive duration of extraction (15- to 25-minute interval) has a significant effect only on the increase of total phenolic content, while specific phenolic compound content and antioxidant capacity were the highest when microwave extraction time of 5 min was applied.

Simultaneous HPLC determination of flavonoids and phenolic acids profile in Pêra-Rio orange juice.

PubMed

Mesquita, E; Monteiro, M

2018-04-01

The aim of this study was to develop and validate an HPLC-DAD method to evaluate the phenolic compounds profile of organic and conventional Pêra-Rio orange juice. The proposed method was validated for 10 flavonoids and 6 phenolic acids. A wide linear range (0.01-223.4μg·g -1 ), good accuracy (79.5-129.2%) and precision (CV≤3.8%), low limits of detection (1-22ng·g -1 ) and quantification (0.7-7.4μg), and overall ruggedness were attained. Good recovery was achieved for all phenolic compounds after extraction and cleanup. The method was applied to organic and conventional Pêra-Rio orange juices from beginning, middle and end of the 2016 harvest. Flavones rutin, nobiletin and tangeretin, and flavanones hesperidin, narirutin and eriocitrin were identified and quantified in all organic and conventional juices. Identity was confirmed by mass spectrometry. Nineteen non-identified phenolic compounds were quantified based on DAD spectra characteristic of the chemical class: 7 cinnamic acid derivatives, 6 flavanones and 6 flavones. The phenolic compounds profile of Pêra-Rio orange juices changed during the harvest; levels increased in organic orange juices, and decreased or were about the same in conventional orange juices. Phenolic compounds levels were higher in organic (0.5-1143.7mg·100g -1 ) than in conventional orange juices (0.5-689.7mg·100g -1 ). PCA differentiated organic from conventional FS and NFC juices, and conventional FCOJ from conventional FS and NFC juices, thus differentiating cultivation and processing. Copyright © 2017. Published by Elsevier Ltd.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Aston, John E.; Apel, William A.; Lee, Brady D.

Alicyclobacillus acidocaldarius, a thermoacidophilic bacterium, has a repertoire of thermo- and acid-stable enzymes that deconstruct lignocellulosic compounds. The work presented here describes the ability of A. acidocaldarius to reduce the concentration of the phenolic compounds: phenol, ferulic acid, ρ-coumaric acid and sinapinic acid during growth conditions. The extent and rate of the removal of these compounds were significantly increased by the presence of micro-molar copper concentrations, suggesting activity by copper oxidases that have been identified in the genome of A. acidocaldarius. Substrate removal kinetics was first order for phenol, ferulic acid, ρ-coumaric acid and sinapinic acid in the presence ofmore » 50 μM copper sulfate. In addition, laccase enzyme assays of cellular protein fractions suggested significant activity on a lignin analog between the temperatures of 45 and 90 °C. As a result, this work shows the potential for A. acidocaldarius to degrade phenolic compounds, demonstrating potential relevance to biofuel production and other industrial processes.« less

[Study of antioxidant activity of phenolic compounds from some species of Georgian flora].

PubMed

Alaniia, M; Shalashvili, K; Sagareishvili, T; Kavtaradze, N; Sutiashvili, M

2013-09-01

The antioxidant activity of extracts obtained from different parts of Georgian flora species Hamamelis virginiana L., Astragalus caucasicus Pall., Astragalus microcephalus Willd., Vitis vinifera L., Rhododendron ponticum L., Rhododendron Ungernii Trautv., Ginkgo biloba L., Salvia officinalis L., Querqus iberica Stev., Maclura aurantiaca Nutt., Cotinus coggygria Ledeb., Fraxinus ornus L., Urtica dioica L., Rhododendron caucasicum Pall., Pueraria hirsuta Matsum., Geranium pusillum L., Astragalus Tanae Sosn., Pinus silvestris L. has been studied. Comparison with ethylentetraacetate and α-tocopherole revealed high efficacy of all extracts studied. 45 individual phenolic compounds were isolated and described by chemical examination of biologically active objects. Common sage (Salvia officinalis) extract turned out as the most active (200 %). The chemical study revealed the dominant content of condensed tannins and low molecular phenolic compounds, which may be attributed to the high antioxidant activity. Biologically active antiatherosclerotic food additive "Salbin" was developed on the basis of Common sage - Salvia officinalis L. phenolic compounds.

Phenolic constituents of shea (Vitellaria paradoxa) kernels.

PubMed

Maranz, Steven; Wiesman, Zeev; Garti, Nissim

2003-10-08

Analysis of the phenolic constituents of shea (Vitellaria paradoxa) kernels by LC-MS revealed eight catechin compounds-gallic acid, catechin, epicatechin, epicatechin gallate, gallocatechin, epigallocatechin, gallocatechin gallate, and epigallocatechin gallate-as well as quercetin and trans-cinnamic acid. The mean kernel content of the eight catechin compounds was 4000 ppm (0.4% of kernel dry weight), with a 2100-9500 ppm range. Comparison of the profiles of the six major catechins from 40 Vitellaria provenances from 10 African countries showed that the relative proportions of these compounds varied from region to region. Gallic acid was the major phenolic compound, comprising an average of 27% of the measured total phenols and exceeding 70% in some populations. Colorimetric analysis (101 samples) of total polyphenols extracted from shea butter into hexane gave an average of 97 ppm, with the values for different provenances varying between 62 and 135 ppm of total polyphenols.

Effect of variety on content of bioactive phenolic compounds in common elder (Sambucus nigra L.).

PubMed

Vrchotová, Naděžda; Dadáková, Eva; Matějíček, Aleš; Tříska, Jan; Kaplan, Jiří

2017-03-01

The inflorescence of common elder (Sambucus nigra L., Adoxaceae) is known to be rich in phenolic compounds. The content of five selected phenolic compounds (rutin, chlorogenic acid, isoquercitrin, isorhamnetin-3-O- rutinoside and dicaffeoylquinic acid) was determined in methanolic extracts from flowers and floral stems by HPLC in samples obtained from 20 varieties of S. nigra cultivated in Czech Republic. In all samples, there were determined rutin (11-54 mg/g), chlorogenic acid (23-46 mg/g), isoquercitrin (0.6-18 mg/g), isorhamnetin-3-O-rutinoside (3-10 mg/g), calculated on air-dried material. The content of dicaffeoylquinic acid was 0-13 mg/g of air-dried material. The amount of the analysed compounds in floral stems was lower than the flowers. The results are a unique set of information on the content of main phenolics in the inflorescence of cultured elderberry varieties.

Phenolic antioxidants from the leaves of Corchorus olitorius L.

PubMed

Azuma, K; Nakayama, M; Koshioka, M; Ippoushi, K; Yamaguchi, Y; Kohata, K; Yamauchi, Y; Ito, H; Higashio, H

1999-10-01

Six phenolic antioxidative compounds [5-caffeoylquinic acid (chlorogenic acid), 3,5-dicaffeoylquinic acid, quercetin 3-galactoside, quercetin 3-glucoside, quercetin 3-(6-malonylglucoside), and quercetin 3-(6-malonylgalactoside) (tentative)] were identified from the leaves of Corchorus olitorius L. (moroheiya) by NMR and FAB-MS. The contents of these phenolic compounds, ascorbic acid, and alpha-tocopherol in C. olitorius leaves were determined, and their antioxidative activities were measured using the radical generator-initiated peroxidation of linoleic acid. The results obtained showed that 5-caffeoylquinic acid was a predominant phenolic antioxidant in C. olitorius leaves.

A theoretical study on predicted protein targets of apple polyphenols and possible mechanisms of chemoprevention in colorectal cancer

PubMed Central

Scafuri, Bernardina; Marabotti, Anna; Carbone, Virginia; Minasi, Paola; Dotolo, Serena; Facchiano, Angelo

2016-01-01

We investigated the potential role of apple phenolic compounds in human pathologies by integrating chemical characterization of phenolic compounds in three apple varieties, computational approaches to identify potential protein targets of the compounds, bioinformatics analyses on data from public archive of gene expression data, and functional analyses to hypothesize the effects of the selected compounds in molecular pathways. Starting by the analytic characterization of phenolic compounds in three apple varieties, i.e. Annurca, Red Delicious, and Golden Delicious, we used computational approaches to verify by reverse docking the potential protein targets of the identified compounds. Direct docking validation of the potential protein-ligand interactions has generated a short list of human proteins potentially bound by the apple phenolic compounds. By considering the known chemo-preventive role of apple antioxidants’ extracts against some human pathologies, we performed a functional analysis by comparison with experimental gene expression data and interaction networks, obtained from public repositories. The results suggest the hypothesis that chemo-preventive effects of apple extracts in human pathologies, in particular for colorectal cancer, may be the interference with the activity of nucleotide metabolism and methylation enzymes, similarly to some classes of anticancer drugs. PMID:27587238

Sustainable biodegradation of phenol by immobilized Bacillus sp. SAS19 with porous carbonaceous gels as carriers.

PubMed

Ke, Qian; Zhang, Yunge; Wu, Xilin; Su, Xiaomei; Wang, Yuyang; Lin, Hongjun; Mei, Rongwu; Zhang, Yu; Hashmi, Muhammad Zaffar; Chen, Chongjun; Chen, Jianrong

2018-09-15

In this study, high-efficient phenol-degrading bacterium Bacillus sp. SAS19 which was isolated from activated sludge by resuscitation-promoting factor (Rpf) addition, were immobilized on porous carbonaceous gels (CGs) for phenol degradation. The phenol-degrading capabilities of free and immobilized Bacillus sp. SAS19 were evaluated under various initial phenol concentrations. The obtained results showed that phenol could be removed effectively by both free and immobilized Bacillus sp. SAS19. Furthermore, for degradation of phenol at high concentrations, long-term utilization and recycling were more readily achieved for immobilized bacteria as compared to free bacteria. Immobilized bacteria exhibited significant increase in phenol-degrading capabilities in the third cycle of recycling and reuse, which demonstrated 87.2% and 100% of phenol (1600 mg/L) degradation efficiency at 12 and 24 h, respectively. The present study revealed that immobilized Bacillus sp. SAS19 can be potentially used for enhanced treatment of synthetic phenol-laden wastewater. Copyright © 2018 Elsevier Ltd. All rights reserved.

Contribution of Polyphenol Oxidation, Chlorophyll and Vitamin C Degradation to the Blackening of Piper nigrum L.

PubMed

Gu, Fenglin; Huang, Feifei; Wu, Guiping; Zhu, Hongying

2018-02-09

Black pepper ( Piper nigrum L.) is the most widely used spice in the world. Blackening is considered to be beneficial and important in the processing of black pepper because it contributes to its color and flavor. The purpose of this paper is to investigate polyphenol oxidation as well as the chlorophyll and vitamin C (VC) degradation in the blackening of Piper nigrum L. Black pepper was produced by four methods, and changes in polyphenols, chlorophyll and VC were studied by high performance liquid chromatography (HPLC) and ultraviolet-visible and visible (UV-Vis) spectrophotometry. The results show that polyphenol oxidase activity significantly decreased during the preparation of black pepper, and the concentrations of phenolic compounds, VC, and chlorophyll a and b also significantly decreased. Polyphenol oxidation and chlorophyll and VC degradation contribute to the blackening. A crude extract of phenolic compounds from black pepper was prepared by the system solvent method. The greater the polarity of the extraction solvent, the higher the extraction rates of the phenolic compounds and the total phenol content. Pepper phenolic compounds were analyzed by HPLC analysis.

Extraction of triterpenoids and phenolic compounds from Ganoderma lucidum: optimization study using the response surface methodology.

PubMed

Oludemi, Taofiq; Barros, Lillian; Prieto, M A; Heleno, Sandrina A; Barreiro, Maria F; Ferreira, Isabel C F R

2018-01-24

The extraction of triterpenoids and phenolic compounds from Ganoderma lucidum was optimized by using the response surface methodology (RSM), using heat and ultrasound assisted extraction techniques (HAE and UAE). The obtained results were compared with that of the standard Soxhlet procedure. RSM was applied using a circumscribed central composite design with three variables (time, ethanol content, and temperature or ultrasonic power) and five levels. The conditions that maximize the responses (extraction yield, triterpenoids and total phenolics) were: 78.9 min, 90.0 °C and 62.5% ethanol and 40 min, 100.0 W and 89.5% ethanol for HAE and UAE, respectively. The latter was the most effective, resulting in an extraction yield of 4.9 ± 0.6% comprising a content of 435.6 ± 21.1 mg g -1 of triterpenes and 106.6 ± 16.2 mg g -1 of total phenolics. The optimized extracts were fully characterized in terms of individual phenolic compounds and triterpenoids by HPLC-DAD-ESI/MS. The recovery of the above-mentioned bioactive compounds was markedly enhanced using the UAE technique.

Ultrasonic-assisted extraction combined with sample preparation and analysis using LC-ESI-MS/MS allowed the identification of 24 new phenolic compounds in pecan nut shell [Carya illinoinensis (Wangenh) C. Koch] extracts.

PubMed

Hilbig, Josiane; Alves, Victor Rodrigues; Müller, Carmen Maria Olivera; Micke, Gustavo Amadeu; Vitali, Luciano; Pedrosa, Rozangela Curi; Block, Jane Mara

2018-04-01

Ultrasonic-assisted extraction combined with statistical tools (factorial design, response surface methodology and kinetics) were used to evaluate the effects of the experimental conditions of temperature, solid-to-solvent ratio, ethanol concentration and time for the extraction of the total phenolic content from pecan nut shells. The optimal conditions for the aqueous and hydroalcoholic extract (with 20% v/v of ethanol) were 60 and 80 °C; solid to solvent ratio of 30 mL·g -1 (for both) and extraction time of 35 and 25 min, respectively. Using these optimize extraction conditions, 426 and 582 mg GAE·g -1 of phenolic compounds, from the aqueous and hydroalcoholic phases respectively, were obtained. In addition, the analysis of the phenolic compounds using the LC-ESI-MS/MS system allowed the identification of 29 phenolic compounds, 24 of which had not been reported in literature for this raw material yet. Copyright © 2018. Published by Elsevier Ltd.

First Approach to the Analytical Characterization of
Barrel-Aged Grape Marc Distillates Using Phenolic Compounds and Colour Parameters

PubMed Central

Rodríguez-Solana, Raquel; Salgado, José Manuel; Domínguez, José Manuel

2014-01-01

Summary Phenolic compounds (benzoic and cinnamic acid derivatives) were determined by high-performance liquid chromatography with multiple wavelength detector (HPLC- -MWD) in grape marc distillates aged in Quercus petraea, Quercus robur and Quercus alba wooden barrels. In addition to colour indices and evaluable polyphenols, all samples were described by sensorial analysis. There were significant differences in the mean concentrations of the majority of phenolic compounds among the samples. Gallic and benzoic acids were the most abundant and samples aged in Q. robur from Galicia (NW of Spain) had the highest concentration of most of the determined phenols. Grape marc distillates aged in Q. robur obtained the highest values of all sensorial attributes, whereas samples aged in Q. petraea and Q. alba obtained similar scores. Principal component analysis accounted for 88.32% of total variance, showing a good separation of aged distillates in terms of phenolic compounds and colour characteristics, according to the species and origin of the oak wood used in the ageing process. PMID:27904312

Carotenoids, Phenolic Compounds and Tocopherols Contribute to the Antioxidative Properties of Some Microalgae Species Grown on Industrial Wastewater.

PubMed

Safafar, Hamed; van Wagenen, Jonathan; Møller, Per; Jacobsen, Charlotte

2015-12-11

This study aimed at investigating the potential of microalgae species grown on industrial waste water as a new source of natural antioxidants. Six microalgae from different classes, including Phaeodactylum sp. (Bacillariophyceae), Nannochloropsis sp. (Eustigmatophyceae), Chlorella sp., Dunaniella sp., and Desmodesmus sp. (Chlorophyta), were screened for their antioxidant properties using different in vitro assays. Natural antioxidants, including pigments, phenolics, and tocopherols, were measured in methanolic extracts of microalgae biomass. Highest and lowest concentrations of pigments, phenolic compounds, and tocopherols were found in Desmodesmus sp. and Phaeodactylum tricornuotom microalgae species, respectively. The results of each assay were correlated to the content of natural antioxidants in microalgae biomass. Phenolic compounds were found as major contributors to the antioxidant activity in all antioxidant tests while carotenoids were found to contribute to the 1,1-diphenyl-2-picryl-hydrazil (DPPH) radical scavenging activity, ferrous reduction power (FRAP), and ABTS-radical scavenging capacity activity. Desmodesmus sp. biomass represented a potentially rich source of natural antioxidants, such as carotenoids (lutein), tocopherols, and phenolic compounds when cultivated on industrial waste water as the main nutrient source.

Carotenoids, Phenolic Compounds and Tocopherols Contribute to the Antioxidative Properties of Some Microalgae Species Grown on Industrial Wastewater

PubMed Central

Safafar, Hamed; van Wagenen, Jonathan; Møller, Per; Jacobsen, Charlotte

2015-01-01

This study aimed at investigating the potential of microalgae species grown on industrial waste water as a new source of natural antioxidants. Six microalgae from different classes, including Phaeodactylum sp. (Bacillariophyceae), Nannochloropsis sp. (Eustigmatophyceae), Chlorella sp., Dunaniella sp., and Desmodesmus sp. (Chlorophyta), were screened for their antioxidant properties using different in vitro assays. Natural antioxidants, including pigments, phenolics, and tocopherols, were measured in methanolic extracts of microalgae biomass. Highest and lowest concentrations of pigments, phenolic compounds, and tocopherols were found in Desmodesmus sp. and Phaeodactylum tricornuotom microalgae species, respectively. The results of each assay were correlated to the content of natural antioxidants in microalgae biomass. Phenolic compounds were found as major contributors to the antioxidant activity in all antioxidant tests while carotenoids were found to contribute to the 1,1-diphenyl-2-picryl-hydrazil (DPPH) radical scavenging activity, ferrous reduction power (FRAP), and ABTS-radical scavenging capacity activity. Desmodesmus sp. biomass represented a potentially rich source of natural antioxidants, such as carotenoids (lutein), tocopherols, and phenolic compounds when cultivated on industrial waste water as the main nutrient source. PMID:26690454

BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds.

PubMed

Bontpart, Thibaut; Cheynier, Véronique; Ageorges, Agnès; Terrier, Nancy

2015-11-01

Phenolic compounds are secondary metabolites involved in several plant growth and development processes, including resistance to biotic and abiotic stresses. The biosynthetic pathways leading to the vast diversity of plant phenolic products often include an acylation step, with phenolic compounds being the donor or acceptor molecules. To date, two acyltransferase families using phenolic compounds as acceptor or donor molecules have been described, with each using a different 'energy-rich' acyl donor. BAHD-acyltransferases, named after the first four biochemically characterized enzymes of the group, use acyl-CoA thioesters as donor molecules, whereas SCPL (Serine CarboxyPeptidase Like)-acyltransferases use 1-O-β-glucose esters. Here, common and divergent specifications found in the literature for both enzyme families were analyzed to answer the following questions. Are both acyltransferases involved in the synthesis of the same molecule (or same group of molecules)? Are both acyltransferases recruited in the same plant? How does the subcellular localization of these enzymes impact metabolite trafficking in plant cells? © 2015 INRA. New Phytologist © 2015 New Phytologist Trust.

HPLC-ESI-QTOF-MS as a powerful analytical tool for characterising phenolic compounds in olive-leaf extracts.

PubMed

Quirantes-Piné, Rosa; Lozano-Sánchez, Jesús; Herrero, Miguel; Ibáñez, Elena; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

2013-01-01

Olea europaea L. leaves may be considered a cheap, easily available natural source of phenolic compounds. In a previous study we evaluated the possibility of obtaining bioactive phenolic compounds from olive leaves by pressurised liquid extraction (PLE) for their use as natural anti-oxidants. The alimentary use of these kinds of extract makes comprehensive knowledge of their composition essential. To undertake a comprehensive characterisation of two olive-leaf extracts obtained by PLE using high-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS). Olive leaves were extracted by PLE using ethanol and water as extraction solvents at 150°C and 200°C respectively. Separation was carried out in a HPLC system equipped with a C₁₈-column working in a gradient elution programme coupled to ESI-QTOF-MS operating in negative ion mode. This analytical platform was able to detect 48 compounds and tentatively identify 31 different phenolic compounds in these extracts, including secoiridoids, simple phenols, flavonoids, cinnamic-acid derivatives and benzoic acids. Lucidumoside C was also identified for the first time in olive leaves. The coupling of HPLC-ESI-QTOF-MS led to the in-depth characterisation of the olive-leaf extracts on the basis of mass accuracy, true isotopic pattern and tandem mass spectrometry (MS/MS) spectra. We may conclude therefore that this analytical tool is very valuable in the study of phenolic compounds in plant matrices. Copyright © 2012 John Wiley & Sons, Ltd.

Natural Mediators in the Oxidation of Polycyclic Aromatic Hydrocarbons by Laccase Mediator Systems

PubMed Central

Johannes, Christian; Majcherczyk, Andrzej

2000-01-01

The oxidation of polycyclic aromatic compounds was studied in systems consisting of laccase from Trametes versicolor and so-called mediator compounds. The enzymatic oxidation of acenaphthene, acenaphthylene, anthracene, and fluorene was mediated by various laccase substrates (phenols and aromatic amines) or compounds produced and secreted by white rot fungi. The best natural mediators, such as phenol, aniline, 4-hydroxybenzoic acid, and 4-hydroxybenzyl alcohol were as efficient as the previously described synthetic compounds ABTS [2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid)] and 1-hydroxybenzotriazole. The oxidation efficiency increased proportionally with the redox potentials of the phenolic mediators up to a maximum value of 0.9 V and decreased thereafter with redox potentials exceeding this value. Natural compounds such as methionine, cysteine, and reduced glutathione, containing sulfhydryl groups, were also active as mediator compounds. PMID:10653713

Anthocyanin, phenolics and antioxidant activity changes in purple waxy corn as affected by traditional cooking.

PubMed

Harakotr, Bhornchai; Suriharn, Bhalang; Tangwongchai, Ratchada; Scott, Marvin Paul; Lertrat, Kamol

2014-12-01

Antioxidant components, including anthocyanins and phenolic compounds, antioxidant activity, and their changes during traditional cooking of fresh purple waxy corn were investigated. As compared to the raw corn, thermal treatment caused significant (p⩽0.05) decreases in each antioxidant compound and antioxidant activity. Steam cooking preserved more antioxidant compounds than boiling. Boiling caused a significant loss of anthocyanin and phenolic compounds into the cooking water. This cooking water is a valuable co-product because it is a good source of purple pigment. By comparing levels of antioxidant compounds in raw and cooked corn, we determined that degradation results in greater loss than leaching or diffusion into cooking water. Additionally, separation of kernels from the cob prior to cooking caused increased loss of antioxidant compounds. Copyright © 2014 Elsevier Ltd. All rights reserved.

Increasing antioxidant activity and reducing decay of blueberries by essential oils.

PubMed

Wang, Chien Y; Wang, Shiow Y; Chen, Chitsun

2008-05-28

Several naturally occurring essential oils including carvacrol, anethole, cinnamaldehyde, cinnamic acid, perillaldehyde, linalool, and p-cymene were evaluated for their effectiveness in reducing decay and increasing antioxidant levels and activities in 'Duke' blueberries ( Vaccinium corymbosum). Carvacrol, anethole, and perillaldehyde showed the capability to promote total anthocyanins and total phenolics and enhance antioxidant activity in fruit tissues expressed as oxygen radical absorbance capacity (ORAC) and hydroxyl radical ( (*)OH) scavenging capacity. All of the essential oils tested in this study were able to inhibit fruit decay development to some degree compared to controls. The most effective compound for mold retardation was p-cymene, followed by linalool, carvacrol, anethole, and perillaldehyde. Cinnamic acid and cinnamaldehyde also suppressed mold growth, but to a lesser extent. Treatment with carvacrol, anethole, or perillaldehyde also significantly increased the levels of fructose, glucose, and citric acid. Individual flavonoids were variably affected by the essential oils. Levels of chlorogenic acid, which was the major phenolic compound in blueberry fruit, were enhanced by all of the essential oils in this study. Increased amounts of quercetin 3-galactoside and quercetin 3-arabinoside were also found in all treated fruit except samples treated with linalool or p-cymene. The major anthocyanin, malvidin 3-galactoside, was enhanced by all essential oils tested except linalool and p-cymene. The levels of other individual anthocyanins including petunidin 3-galactoside, delphinidin 3-galactoside, petunidin 3-glucoside, petunidin 3-arabinoside, delphinidin 3-arabinoside, and cyanidin 3-galactoside were higher in treated fruit compared to controls. Those essential oils that have positive effects on enhancing anthocyanins, phenolic compounds, and antioxidant activity of fruit, but inhibitory effects on microbial growth and decay development, deserve further evaluation.

Defence response of tomato seedlings to oxidative stress induced by phenolic compounds from dry olive mill residue.

PubMed

García-Sánchez, Mercedes; Garrido, Inmaculada; Casimiro, Ilda de Jesús; Casero, Pedro Joaquín; Espinosa, Francisco; García-Romera, Inmaculada; Aranda, Elisabet

2012-10-01

ADOR is an aqueous extract obtained from the dry olive mill residue (DOR) which contains the majority of its soluble phenolic compounds, which are responsible for its phytotoxic properties. Some studies have shown that ADOR negatively affects seed germination. However, to date, few studies have been carried out on the effect of ADOR on the oxidative stress of the plant. It is well known that saprobe fungi can detoxify these phenolic compounds and reduce the potential negative effects of ADOR on plants. To gain a better understanding of the phytotoxic effects and oxidative stress caused by this residue, tomato seeds were germinated in the presence of ADOR, treated and untreated with Coriolopsis rigida, Trametes versicolor, Pycnoporus cinnabarinus and Penicillium chrysogenum-10 saprobe fungi. ADOR sharply reduced tomato seed germination and also generated high levels of malondialdehyde (MDA), O(2)(-) and H(2)O(2). However, bioremediated ADOR did not negatively affect germination and reduced MDA, O(2)(-) and H(2)O(2) content in different ways depending on the fungus used. In addition, the induced defense response was studied by analyzing the activity of both antioxidant enzymes (superoxide dismutase (SOD), catalase, ascorbate peroxidasa, glutathione reductase (GR), peroxidases and coniferil alcohol peroxidasa) and detoxification enzymes (glutathione-S-transferase (GST)). Our findings suggest that, because ADOR is capable of inducing oxidative stress, tomato seedlings trigger a defense response through SOD, GR, and GST activity and through antioxidant and lignification processes. On the other hand, the bioremediation of ADOR plays an important role in counteracting the oxidative stress induced by the untreated residue. Copyright © 2012 Elsevier Ltd. All rights reserved.

Hydrothermal degradation of lignin: products analysis for phenol formaldehyde adhesive synthesis.

PubMed

Yang, Sheng; Yuan, Tong-Qi; Li, Ming-Fei; Sun, Run-Cang

2015-01-01

Corncob lignin was treated with pressurized hot water in a cylindrical autoclave in current investigation. With the aim of investigating the effect of reaction temperature and retention time on the distribution of degradation products, the products were divided into five fractions including gas, volatile organic compounds, water-soluble oil, heavy oil, and solid residue. It was found that hydrothermal degradation of corncob lignin in pressurized hot water produced a large amount of phenolic compounds with lower molecular weight than the raw lignin. Some phenolic and benzene derivatives monomers such as vanillin, 2-methoxy-phenol, 2-ethyl-phenol, p-xylene, and 1, 3-dimethyl-benzene were also identified in the degradation products. The products were further analyzed by GC-MS, GPC, 2D-HSQC, and (31)P-NMR to investigate their suitability for partial incorporation into phenol formaldehyde adhesive as a substitution of phenol. The results indicated that the reaction temperature had more effect on the products distribution than the retention time. The optimal condition for heavy oil production appeared at 290 °C with retention time 0 min. The compounds of heavy oil had more active sites than the raw lignin, suggesting that the heavy oil obtained from hydrothermal degradation of lignin is a promising material for phenol formaldehyde adhesive synthesis. Copyright © 2014 Elsevier B.V. All rights reserved.

Control of occupational exposure to phenol in industrial wastewater treatment plant of a petroleum refinery in Alexandria, Egypt: An intervention application case study.

PubMed

Zaki, Gehan R; El-Marakby, Fadia A; Ramadan, Alaa El-Din K; Issa, Ahmed I; Nofal, Faten H

2016-11-01

Phenol exposure is one of the hazards in the industrial wastewater treatment basin of any refinery. It additively interacts with hydrogen sulfide emitted from the wastewater basin. Consequently, its concentration should be greatly lower than its threshold limit value. The present study aimed at controlling occupational exposure to phenol in the work environment of wastewater treatment plant in a refinery by reducing phenolic compounds in the industrial wastewater basin. This study was conducted on both laboratory and refinery scales. The first was completed by dividing each wastewater sample from the outlets of different refinery units into three portions; the first was analyzed for phenolic compounds. The second and third were for laboratory scale charcoal and bacterial treatments. The two methods were compared regarding their simplicities, design, and removal efficiencies. Accordingly, bacterial treatment by continuous flow of sewage water containing Pseudomonas Aeruginosa was used for refinery scale treatment. Laboratory scale treatment of phenolic compounds revealed higher removal efficiency of charcoal [100.0(0.0) %] than of bacteria [99.9(0.013) %]. The refinery scale bacterial treatment was [99.8(0.013) %] efficient. Consequently, level of phenol in the work environment after refinery-scale treatment [0.069(0.802) mg/m(3)] was much lower than that before [5.700(26.050) mg/m(3)], with removal efficiency of [99.125(2.335) %]. From the present study, we can conclude that bacterial treatment of phenolic compounds in industrial wastewater of the wastewater treatment plant using continuous flow of sewage water containing Pseudomonas Aeruginosa reduces the workers' exposure to phenol.

Phenol and terpene quenching of singlet- and triplet-excited states of riboflavin in relation to light-struck flavor formation in beer.

PubMed

Cardoso, Daniel R; Olsen, Karsten; Møller, Jens K S; Skibsted, Leif H

2006-07-26

Phenolic compounds present in beer were shown by fluorescence spectroscopy and laser flash photolysis to deactivate both singlet- and triplet-excited states of riboflavin with bimolecular rate constants close to the diffusion control ranging from 2.8x10(9) to 1.1x10(10) M-1 s-1 and from 1.1x10(9) to 2.6x10(9) M-1 s-1, respectively. Enthalpies of activation were low (up to 33.2 kJ mol-1), and entropies of activation were positive, ranging from 17 to 92 J mol-1 K-1, as derived from temperature dependence, indicating a compensation effect. From a Stern-Volmer analysis of the singlet-excited riboflavin quenching by phenols it was found that high amounts of phenolic compounds (>0.3 M) would be needed to hinder triplet-excited riboflavin generation. On the other hand, a phenolic content of 0.36 mM is likely to quench 90% of the triplet-excited state. Phenol photodegradation was found to be complex, and using ESI-MS analysis it was not possible to identify specific photooxidation products of the phenolic compounds; only the photoproducts of riboflavin could be detected and structurally assigned. The rate of reaction of triplet-excited riboflavin with phenolic compounds in acetonitrile/citrate buffer (pH 4.6, 10 mM) is 550 times faster than the reaction with iso-alpha-acids from hops, indicating that triplet-excited quenchers such as phenols may be involved in the early steps in light-struck flavor formation in beer through radical formation. Terpenes present in herb-flavored beers were found to be nonreactive toward singlet- and triplet-excited-state riboflavin, and any protection depends on other mechanisms.

GC-MS olfactometric and LC-DAD-ESI-MS/MS characterization of key odorants and phenolic compounds in black dry-salted olives.

PubMed

Selli, Serkan; Kelebek, Hasim; Kesen, Songul; Sonmezdag, Ahmet Salih

2018-02-01

Olives are processed in different ways depending on consumption habits, which vary between countries. Different de-bittering methods affect the aroma and aroma-active compounds of table olives. This study focused on analyzing the aroma and aroma-active compounds of black dry-salted olives using gas chromatography-mass spectrometry-olfactometry (GC-MS-O) techniques. Thirty-nine volatile compounds which they have a total concentration of 29 459 µg kg -1 , were determined. Aroma extract dilution analysis (AEDA) was used to determine key aroma compounds of table olives. Based on the flavor dilution (FD) factor, the most powerful aroma-active compounds in the sample were methyl-2-methyl butyrate (tropical, sweet; FD: 512) and (Z)-3-hexenol (green, flowery; FD: 256). Phenolic compounds in table olives were also analyzed by LC-DAD-ESI-MS/MS. A total of 20 main phenolic compounds were identified and the highest content of phenolic compound was luteolin-7-glucoside (306 mg kg -1 ), followed by verbascoside (271 mg kg -1 ), oleuropein (231 mg kg -1 ), and hydroxytyrosol (3,4-DHPEA) (221 mg kg -1 ). Alcohols, carboxylic acids, and lactones were qualitatively and quantitatively the dominant volatiles in black dry-salted olives. Results indicated that esters and alcohols were the major aroma-active compounds. © 2018 Society of Chemical Industry. © 2018 Society of Chemical Industry.

Optimization of extraction conditions of total phenolics, antioxidant activities, and anthocyanin of oregano, thyme, terebinth, and pomegranate.

PubMed

Rababah, Taha M; Banat, Fawzi; Rababah, Anfal; Ereifej, Khalil; Yang, Wade

2010-09-01

The purpose of this study was to evaluate the total phenolic extracts and antioxidant activity and anthocyanins of varieties of the investigated plants. These plants include oregano, thyme, terebinth, and pomegranate. The optimum extraction conditions including temperature and solvent of the extraction process itself were investigated. Total phenolic and anthocyanin extracts were examined according to Folin-Ciocalteu assay and Rabino and Mancinelli method, respectively. The effect of different extracting solvents and temperatures on extracts of phenolic compounds and anthocyanins were studied. Plant samples were evaluated for their antioxidant chemical activity by 2, 2-diphenyl-1-picrylhydrazl assay, to determine their potential as a source of natural antioxidant. Results showed that all tested plants exhibited appreciable amounts of phenolic compounds. The methanolic extract (60 °C) of sour pomegranate peel contained the highest phenolic extract (4952.4 mg/100 g of dry weight). Terebinth green seed had the lowest phenolic extract (599.4 mg/100 g of dry weight). Anthocyanins ranged between 3.5 (terebinth red seed) and 0.2 mg/100 g of dry material (thyme). Significant effect of different extracting solvents and temperatures on total phenolics and anthocyanin extracts were found. The methanol and 60 °C of extraction conditions found to be the best for extracting phenolic compounds. The distilled water and 60 °C extraction conditions found to be the best for extracting anthocyanin.

Variation in Phenolics, Flavanoids, Antioxidant and Tyrosinase Inhibitory Activity of Peach Blossoms at Different Developmental Stages.

PubMed

Liu, Jie-Chao; Jiao, Zhong-Gao; Yang, Wen-Bo; Zhang, Chun-Ling; Liu, Hui; Lv, Zhen-Zhen

2015-11-18

Peach blossoms were harvested and classified into six developmental stages: (I) bud emerging stage; (II) middle bud stage; (III) large bud stage; (IV) initial-flowering stage; (V) full-flowering stage; and (VI) end-flowering stage. The contents of total phenolics, flavanoids, individual phenolic compounds as well as antioxidant and tyrosinase inhibitory activity of peach blossoms at different developmental stages were investigated. The total phenolic contents varied from 149.80 to 74.80 mg chlorogenic acid equivalents/g dry weight (DW), and the total flavanoid contents ranged from 93.03 to 44.06 mg rutin equivalents/g DW. Both the contents of total phenolics and flavanoids decreased during blossom development. Chlorogenic acid was the predominant component, accounting for 62.08%-71.09% of the total amount of identified phenolic compounds in peach blossom. The antioxidant capacities determined by different assays and tyrosinase inhibitory activity also showed descending patterns during blossom development. Significant correlations were observed between antioxidant capacities with contents of total phenolics and total flavanoids as well as chlorogenic acid, cinnamic acid and kaempferol-3-O-galactoside, while the tyrosinase inhibitory activity had lower correlations with total phenolics and total flavanoids as well as chlorogenic acid, quercetin-3-O-rhamnoside, kaempferol-3-O-galactoside and cinnamic acid. The antioxidant activities of peach blossom seemed to be more dependent on the phenolic compounds than tyrosinase inhibitory activity.

Biological abatement of enzyme inhibitors

USDA-ARS?s Scientific Manuscript database

Lignocellulose pretreatments release phenolic compounds that cause enzyme inhibition and deactivation. Bio-abatement, the biological removal of furfurals, acetic acid and phenolics, may utilize fungal fermentation to metabolize these compounds to CO2, water, cell mass, and heat. Our work with Coni...

A Phenolic Extract Obtained from Methyl Jasmonate-Treated Strawberries Enhances Apoptosis in a Human Cervical Cancer Cell Line.

PubMed

Spagnuolo, Carmela; Flores, Gema; Russo, Gian Luigi; Ruiz Del Castillo, Maria Luisa

2016-10-01

In the present study, we evaluated the effect of methyl jasmonate (MeJA) treatment on strawberry phenolic composition. Strawberry extracts contain a mixture of phenolic compounds possessing several biological properties. We demonstrated that these extracts were more effective in inducing apoptosis in HeLa cells compared to phenolic preparations derived from untreated strawberries. Treatment of strawberries with 0.5% MeJA resulted in increased polyphenols content (from 7.4 to 8.6 mM quercetin equivalents) and antioxidant properties (from 3.9 to 4.6 mM quercetin equivalents). The identification and quantification of phenolic compounds by liquid chromatography-mass spectrometry in the strawberry extracts showed that cyanidin glucoside, pelargonidin glucoside, and ellagic glucoside acid were significantly higher in strawberries treated with MeJA. Phenolic extracts from MeJA-treated strawberries significantly decreased the cell viability in HeLa cells, compared to extracts derived from untreated fruits. We hypothesized that the enhanced apoptotic activity of MeJA-treated strawberries was due to a synergistic or additive effect of different phenolic compounds present in the extract, rather than the activity of a single molecule.

Extraction of valuable compounds from mangosteen pericarps by hydrothermal assisted sonication

NASA Astrophysics Data System (ADS)

Machmudah, Siti; Lestari, Sarah Duta; Shiddiqi, Qifni Yasa'Ash; Widiyastuti, Winardi, Sugeng; Wahyudiono, Kanda, Hideki; Goto, Motonobu

2015-12-01

Valuable compounds, such as xanthone and phenolic compounds, from mangosteen pericarps was extracted by hydrothermal treatment at temperatures of 120-160 °C and pressures of 5 MPa using batch and semi-batch extractor. This method is a simple and environmentally friendly extraction method requiring no chemicals other than water. Under these conditions, there is possibility for the formation of phenolic compounds from mangosteen pericarps from decomposition of bounds between lignin, cellulose, and hemicellulose via autohydrolysis. In order to increase the amount of extracted valuable compounds, sonication pre-treament was performed prior to the hydrothermal extraction process. 30 min of sonication pre-treatment could increase significantly the amount of xanthone and phenolic compounds mangosteen pericarps extraction. In batch-system, the xanthone recovery approach to 100 % at 160 °C with 30 min sonication pre-treatment for 150 min extraction time. Under semi-batch process, the total phenolic compounds in the extract was 217 mg/g sample at 160 °C with 30 min sonication pre-treatment for 150 min total extraction time. The results revealed that hydrothermal extraction assisted sonication pre-treatment is applicable method for the isolation of polyphenolic compounds from other types of biomass and may lead to an advanced plant biomass components extraction technology.

Antioxidant and biological properties of bioactive phenolic compounds from Quercus suber L.

PubMed

Fernandes, Ana; Fernandes, Iva; Cruz, Luís; Mateus, Nuno; Cabral, Miguel; de Freitas, Victor

2009-12-09

Phenolic compounds, namely, hydrolyzable tannins and low molecular weight phenolic compounds, were isolated and purified from Portuguese cork from Quercus suber L. Some of these compounds were studied to evaluate their antioxidant activity, including free-radical scavenging capacity (DPPH method) and reducing capacity (FRAP method). All compounds tested showed significant antioxidant activity, namely, antiradical and reducing properties. The antiradical capacity seemed to increase with the presence of galloyl groups. Regarding the reducing capacity, this structure-activity relationship was not so clear. These compounds were also studied to evaluate the growth inhibitory effect on the estrogen responsive human breast cancer cell line (ER+) MCF-7 and two other colon cancer cell lines (Caco-2 and HT-29). Generally, all the compounds tested exhibited, after a continuous exposure during a 48 h period, a dose-dependent growth inhibitory effect. Relative inhibitory activity was primarily related to the number of phenolic hydroxyl groups (galloyl and HHDP moieties) found in the active structures, with more groups generally conferring increased effects, except for HHDP-di-galloyl-glucose. Mongolicain B showed a greater potential to inhibit the growth of the three cell lines tested, identical to the effect observed with castalagin. Since these compounds are structurally related with each other, this activity might be based within the C-glycosidic ellagitannin moiety.

Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry.

PubMed

Borrás Linares, I; Arráez-Román, D; Herrero, M; Ibáñez, E; Segura-Carretero, A; Fernández-Gutiérrez, A

2011-10-21

In the present work, a comparative study between two environmentally friendly and selective extraction techniques, such as supercritical fluid extraction (SFE) and pressurized liquid extraction (PLE) have been carried out focusing in the bioactive phenolic compounds present in Rosmarinus officinalis. For the analysis of the SFE and PLE extracts, a new methodology for qualitative characterization has been developed, based on the use of reversed-phase high-performance liquid chromatography (RP-HPLC), equipped with two different detection systems coupled in series: diode array detector (DAD) and time of flight mass spectrometry (TOF-MS) detector connected via an electrospray ionization interface (ESI). The use of a small particle size C(18) column (1.8 μm) provided a great resolution and made possible the separation of several isomers. Moreover, UV-visible spectrophotometry is a valuable tool for identifying the class of phenolic compounds, whereas MS data enabled to structurally characterize the compounds present in the extracts. The applied methodology was useful for the determination of many well-known phenolic compounds present in R. officinalis, such as carnosol, carnosic acid, rosmadial, rosmanol, genkwanin, homoplantaginin, scutellarein, cirsimaritin and rosmarinic acid, as well as other phenolic compounds present in other species belonging to Lamiaceae family. Copyright © 2011 Elsevier B.V. All rights reserved.

Low cost biosorbent "banana peel" for the removal of phenolic compounds from olive mill wastewater: kinetic and equilibrium studies.

PubMed

Achak, M; Hafidi, A; Ouazzani, N; Sayadi, S; Mandi, L

2009-07-15

The aim of this work is to determine the potential of application of banana peel as a biosorbent for removing phenolic compounds from olive mill wastewaters. The effect of adsorbent dosage, pH and contact time were investigated. The results showed that the increase in the banana peel dosage from 10 to 30 g/L significantly increased the phenolic compounds adsorption rates from 60 to 88%. Increase in the pH to above neutrality resulted in the increase in the phenolic compounds adsorption capacity. The adsorption process was fast, and it reached equilibrium in 3-h contact time. The Freundlich and Langmuir adsorption models were used for mathematical description of the adsorption equilibrium and it was found that experimental data fitted very well to both Freundlich and Langmuir models. Batch adsorption models, based on the assumption of the pseudo-first-order, pseudo-second-order and intraparticle diffusion mechanism, showed that kinetic data follow closely the pseudo-second-order than the pseudo-first-order and intraparticle diffusion. Desorption studies showed that low pH value was efficient for desorption of phenolic compounds. These results indicate clearly the efficiency of banana peel as a low-cost solution for olive mill wastewaters treatment and give some preliminary elements for the comprehension of the interactions between banana peel as a bioadsorbent and the very polluting compounds from the olive oil industry.

Oxidation of a non-phenolic lignin model compound by two Irpex lacteus manganese peroxidases: evidence for implication of carboxylate and radicals.

PubMed

Qin, Xing; Sun, Xianhua; Huang, Huoqing; Bai, Yingguo; Wang, Yuan; Luo, Huiying; Yao, Bin; Zhang, Xiaoyu; Su, Xiaoyun

2017-01-01

Manganese peroxidase is one of the Class II fungal peroxidases that are able to oxidize the low redox potential phenolic lignin compounds. For high redox potential non-phenolic lignin degradation, mediators such as GSH and unsaturated fatty acids are required in the reaction. However, it is not known whether carboxylic acids are a mediator for non-phenolic lignin degradation. The white rot fungus Irpex lacteus is one of the most potent fungi in degradation of lignocellulose and xenobiotics. Two manganese peroxidases ( Il MnP1 and Il MnP2) from I. lacteus CD2 were over-expressed in Escherichia coli and successfully refolded from inclusion bodies. Both Il MnP1 and Il MnP2 oxidized the phenolic compounds efficiently. Surprisingly, they could degrade veratryl alcohol, a non-phenolic lignin compound, in a Mn 2+ -dependent fashion. Malonate or oxalate was found to be also essential in this degradation. The oxidation of non-phenolic lignin was further confirmed by analysis of the reaction products using LC-MS/MS. We proved that Mn 2+ and a certain carboxylate are indispensable in oxidation and that the radicals generated under this condition, specifically superoxide radical, are at least partially involved in lignin oxidative degradation. Il MnP1 and Il MnP2 can also efficiently decolorize dyes with different structures. We provide evidence that a carboxylic acid may mediate oxidation of non-phenolic lignin through the action of radicals. MnPs, but not LiP, VP, or DyP, are predominant peroxidases secreted by some white rot fungi such as I. lacteus and the selective lignocellulose degrader Ceriporiopsis subvermispora . Our finding will help understand how these fungi can utilize MnPs and an excreted organic acid, which is usually a normal metabolite, to efficiently degrade the non-phenolic lignin. The unique properties of Il MnP1 and Il MnP2 make them good candidates for exploring molecular mechanisms underlying non-phenolic lignin compounds oxidation by MnPs and for applications in lignocellulose degradation and environmental remediation.

Effects of cooking methods on phenolic compounds in xoconostle (Opuntia joconostle).

PubMed

Cortez-García, Rosa María; Ortiz-Moreno, Alicia; Zepeda-Vallejo, Luis Gerardo; Necoechea-Mondragón, Hugo

2015-03-01

Xoconostle, the acidic cactus pear fruit of Opuntia joconostle of the Cactaceae family, is the source of several phytochemicals, such as betalain pigments and numerous phenolic compounds. The aim of the present study was to analyze the effect of four cooking procedures (i.e., boiling, grilling, steaming and microwaving) on the total phenolic content (TPC) and antioxidant activity (measured by ABTS, DPPH, reducing power, and BCBA) of xoconostle. In addition, HPLC-DAD analyses were performed to identify and quantify individual phenolic compounds. After microwaving and steaming xoconostle, the TPC remained the same that in fresh samples, whereas both grilling and boiling produced a significant, 20% reduction (p ≤ 0.05). Total flavonoids remained unchanged in boiled and grilled xoconostle, but steaming and microwaving increased the flavonoid content by 13 and 20%, respectively. Steaming and microwaving did not produce significant changes in the antioxidant activity of xoconostle, whereas boiling and grilling result in significant decreases. The phenolic acids identified in xoconostle fruits were gallic, vanillic, 4-hydroxybenzoic, syringic, ferulic and protocatechuic acids; the flavonoids identified were epicatechin, catechin, rutin, quercitrin, quercetin and kaempferol. Based on the results, steaming and microwaving are the most suitable methods for retaining the highest level of phenolic compounds and flavonoids in xoconostle.

The Profile and Bioaccessibility of Phenolic Compounds in Cereals Influenced by Improved Extrusion Cooking Treatment

PubMed Central

Zeng, Zicong; Liu, Chengmei; Luo, Shunjing; Chen, Jun; Gong, Ersheng

2016-01-01

The aim of this study was to investigate the effect of Improved Extrusion Cooking Treatment (IECT) on the phenolics and its bioaccessibility in cereals, represented by brown rice, wheat, and oat. Data showed that total phenolic content and total antioxidant activity in free form were significantly decreased, while the bound form was increased after IECT. After IECT, the total free phenolic acids of brown rice and wheat were significantly decreased by 5.88% and 45.66%, respectively, while the total bound phenolic acids of brown rice, wheat, and oat were significantly increased by 6.45%, 8.78%, and 9.10%, respectively. Brown rice provided the most bioaccessible phenolics and antioxidant compounds, followed by oat and wheat. IECT significantly decreased the bioaccessible phenolics of brown rice and oat by 31.09% and 30.95%, while it had minimal effect on the bioaccessible phenolics of wheat. These results showed that IECT greatly affected the phenolics and its bioaccessibiltiy of cereals, with the effect depending on cereal matrix and the sensitivity of free and bound phenolics. Furthermore, bioaccessible phenolic acids of raw and processed cereals were considerably low, and it slightly contributed to the bioaccessible phenolics. PMID:27513581

Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth.

PubMed

Seal, Alexa N; Haig, Terry; Pratley, James E

2004-08-01

In previous studies, 15 putative allelopathic compounds detected in rice root exudates were quantified by GC/MS/MS. In this study, multiple regression analysis on these compounds determined that five selected phenolics, namely caffeic, p-hydroxybenzoic, vanillic, syringic, and p-coumaric acids, from rice exudates were best correlated with the observed allelopathic effect on arrowhead (Sagittaria montevidensis) root growth. Despite this positive association, determination of the phenolic acid dose-response curve established that the amount quantified in the exudates was much lower than the required threshold concentration for arrowhead inhibition. A similar dose-response curve resulted from a combination of all 15 quantified compounds. Significant differences between the amounts of trans-ferulic acid, abietic acid, and an indole also existed between allelopathic and non-allelopathic rice cultivars. The potential roles of these three compounds in rice allelopathy were examined by chemoassay. Overall, neither the addition of trans-ferulic acid nor 5-hydroxyindole-3-acetic acid to the phenolic mix significantly contributed to phytotoxicity, although at higher concentrations, trans-ferulic acid appeared to act antagonistically to the phytotoxic effects of the phenolic mix. The addition of abietic acid also decreased the inhibitory effect of the phenolic mix. These studies indicate that the compounds quantified are not directly responsible for the observed allelopathic response. It is possible that the amount of phenolic acids may be indirectly related to the chemicals finally responsible for the observed allelopathic effect.

Phenolic compounds in ectomycorrhizal interaction of lignin modified silver birch

PubMed Central

Sutela, Suvi; Niemi, Karoliina; Edesi, Jaanika; Laakso, Tapio; Saranpää, Pekka; Vuosku, Jaana; Mäkelä, Riina; Tiimonen, Heidi; Chiang, Vincent L; Koskimäki, Janne; Suorsa, Marja; Julkunen-Tiitto, Riitta; Häggman, Hely

2009-01-01

Background The monolignol biosynthetic pathway interconnects with the biosynthesis of other secondary phenolic metabolites, such as cinnamic acid derivatives, flavonoids and condensed tannins. The objective of this study is to evaluate whether genetic modification of the monolignol pathway in silver birch (Betula pendula Roth.) would alter the metabolism of these phenolic compounds and how such alterations, if exist, would affect the ectomycorrhizal symbiosis. Results Silver birch lines expressing quaking aspen (Populus tremuloides L.) caffeate/5-hydroxyferulate O-methyltransferase (PtCOMT) under the 35S cauliflower mosaic virus (CaMV) promoter showed a reduction in the relative expression of a putative silver birch COMT (BpCOMT) gene and, consequently, a decrease in the lignin syringyl/guaiacyl composition ratio. Alterations were also detected in concentrations of certain phenolic compounds. All PtCOMT silver birch lines produced normal ectomycorrhizas with the ectomycorrhizal fungus Paxillus involutus (Batsch: Fr.), and the formation of symbiosis enhanced the growth of the transgenic plants. Conclusion The down-regulation of BpCOMT in the 35S-PtCOMT lines caused a reduction in the syringyl/guaiacyl ratio of lignin, but no significant effect was seen in the composition or quantity of phenolic compounds that would have been caused by the expression of PtCOMT under the 35S or UbB1 promoter. Moreover, the detected alterations in the composition of lignin and secondary phenolic compounds had no effect on the interaction between silver birch and P. involutus. PMID:19788757

Phenolic Compounds from Olea europaea L. Possess Antioxidant Activity and Inhibit Carbohydrate Metabolizing Enzymes In Vitro.

PubMed

Dekdouk, Nadia; Malafronte, Nicola; Russo, Daniela; Faraone, Immacolata; De Tommasi, Nunziatina; Ameddah, Souad; Severino, Lorella; Milella, Luigi

2015-01-01

Phenolic composition and biological activities of fruit extracts from Italian and Algerian Olea europaea L. cultivars were studied. Total phenolic and tannin contents were quantified in the extracts. Moreover 14 different phenolic compounds were identified, and their profiles showed remarkable quantitative differences among analysed extracts. Moreover antioxidant and enzymatic inhibition activities were studied. Three complementary assays were used to measure their antioxidant activities and consequently Relative Antioxidant Capacity Index (RACI) was used to compare and easily describe obtained results. Results showed that Chemlal, between Algerian cultivars, and Coratina, among Italian ones, had the highest RACI values. On the other hand all extracts and the most abundant phenolics were tested for their efficiency to inhibit α-amylase and α-glucosidase enzymes. Leccino, among all analysed cultivars, and luteolin, among identified phenolic compounds, were found to be the best inhibitors of α-amylase and α-glucosidase enzymes. Results demonstrated that Olea europaea fruit extracts can represent an important natural source with high antioxidant potential and significant α-amylase and α-glucosidase inhibitory effects.

The effects of plant growth regulators and L-phenylalanine on phenolic compounds of sweet basil.

PubMed

Koca, Nülüfer; Karaman, Şengül

2015-01-01

The effects of methyl jasmonate (MeJA), spermine (Spm), epibrassinolide (EBL) and l-phenylalanine on sweet basil (Ocimum basilicum L.) were studied to determine the amount of phenolic compounds and enzymatic activity of phenylalanine ammonia-lyase (PAL). Total phenolic and total flavonoid contents of sweet basils were determined by a spectrophotometer, and individual phenolic compounds and activity of PAL were analysed by HPLC/UV. The highest total phenolic (6.72 mg GAE/g) and total flavonoid contents (0.92 mg QE/g) obtained from 1.0 mM Spm+MeJA application. Rosmarinic acid (RA) and caffeic acid contents significantly enhanced after the applications but no such differences observed in chicoric acid content or PAL activity. RA was the main phenolic acid in all samples and its concentration varied from 1.04 to 2.70 mg/gFW. As a result the combinations of Spm+MeJA and EBL+MeJA can induce secondary metabolites effectively and those interactions play important role in the production of phytochemicals in plants. Copyright © 2014 Elsevier Ltd. All rights reserved.

Phenolic Compounds from Olea europaea L. Possess Antioxidant Activity and Inhibit Carbohydrate Metabolizing Enzymes In Vitro

PubMed Central

Dekdouk, Nadia; Malafronte, Nicola; Russo, Daniela; Faraone, Immacolata; Ameddah, Souad; Severino, Lorella

2015-01-01

Phenolic composition and biological activities of fruit extracts from Italian and Algerian Olea europaea L. cultivars were studied. Total phenolic and tannin contents were quantified in the extracts. Moreover 14 different phenolic compounds were identified, and their profiles showed remarkable quantitative differences among analysed extracts. Moreover antioxidant and enzymatic inhibition activities were studied. Three complementary assays were used to measure their antioxidant activities and consequently Relative Antioxidant Capacity Index (RACI) was used to compare and easily describe obtained results. Results showed that Chemlal, between Algerian cultivars, and Coratina, among Italian ones, had the highest RACI values. On the other hand all extracts and the most abundant phenolics were tested for their efficiency to inhibit α-amylase and α-glucosidase enzymes. Leccino, among all analysed cultivars, and luteolin, among identified phenolic compounds, were found to be the best inhibitors of α-amylase and α-glucosidase enzymes. Results demonstrated that Olea europaea fruit extracts can represent an important natural source with high antioxidant potential and significant α-amylase and α-glucosidase inhibitory effects. PMID:26557862

Pervaporation of phenols

DOEpatents

Boddeker, Karl W.

1989-01-01

Aqueous phenolic solutions are separated by pervaporation to yield a phenol-depleted retentate and a phenol-enriched permeate. The separation effect is enhanced by phase segregation into two immiscible phases, "phenol in water" (approximately 10% phenol), and "water in phenol" (approximately 70% phenol). Membranes capable of enriching phenols by pervaporation include elastomeric polymers and anion exchange membranes, membrane selection and process design being guided by pervaporation performance and chemical stability towards phenolic solutions. Single- and multiple-stage procresses are disclosed, both for the enrichment of phenols and for purification of water from phenolic contamination.

Pervaporation of phenols

DOEpatents

Boddeker, K.W.

1989-02-21

Aqueous phenolic solutions are separated by pervaporation to yield a phenol-depleted retentate and a phenol-enriched permeate. The separation effect is enhanced by phase segregation into two immiscible phases, phenol in water'' (approximately 10% phenol), and water in phenol'' (approximately 70% phenol). Membranes capable of enriching phenols by pervaporation include elastomeric polymers and anion exchange membranes, membrane selection and process design being guided by pervaporation performance and chemical stability towards phenolic solutions. Single- and multiple-stage processes are disclosed, both for the enrichment of phenols and for purification of water from phenolic contamination. 8 figs.

Molecularly imprinted polymers as a tool for the study of the 4-ethylphenol metabolic pathway in red wines.

PubMed

Garcia, Deiene; Gomez-Caballero, Alberto; Guerreiro, Antonio; Goicolea, M Aranzazu; Barrio, Ramon J

2015-09-04

A molecularly imprinted polymer (MIP) based methodology is described here for the determination of compounds that belong to the 4-ethylphenol (4EP) metabolic pathway in red wines. To this end, two MIP materials have been developed: a 4EP MIP as a class-selective material to extract phenols that belong to the 4EP metabolic pathway and a coumaric acid (CA) imprinted polymer as a MIP-based stationary phase capable of selectively separating these phenols on HPLC analysis, obtaining clean chromatograms. 4-vinyl pyridine and ethylene glycol dimethacrylate were respectively used as functional monomer and cross-linker for both MIPs. Once polymer compositions were optimised, the 4EP MIP was packed into SPE cartridges for wine sample clean-up and CA MIP was packed into HPLC columns to chromatographically separate the compounds present in the eluates obtained after SPE extraction. The accuracy of the proposed method was tested spiking wine samples with known concentrations of target compounds and subsequently, analytes were quantified by the standard addition method. Registered mean recoveries ranged from 95.2 to 109.2% and RSD values were below 10% in most cases. The described methodology was found to be suitable for the selective extraction and quantification of the compounds that belong to the 4EP metabolic pathway in red wines with minimal matrix effects and could be undoubtedly exploited to monitor 4EP and its precursors in wines. Copyright © 2015 Elsevier B.V. All rights reserved.

Treatment of wastewater streams containing phenolic compounds using hybrid techniques based on cavitation: a review of the current status and the way forward.

PubMed

Gogate, Parag R

2008-01-01

Phenolic compounds, including its chloro and nitro derivatives, contribute significantly to environmental hazards due to high degree of toxicity as well as improper disposal methods. Cavitation can be used for degradation of phenolic compounds and recently Kidak and Ince [R. Kidak, N.H. Ince, Ultrason. Sonochem. 13 (2006) 195] have given an interesting review on the application of cavitation for destruction of phenolic compounds. A main finding of their work and generally accepted fact is that cavitation alone cannot be an economical technique for wastewater treatment. The present work overviews the different ways in which the cavitation phenomena can be intensified by using additives and/or combining cavitation with other oxidation processes. Hybrid methods viz. Ultrasound/H2O2 or ozone, cavitation assisted by use of catalysts/additives, sonophotocatalytic oxidation and cavitation coupled with biological oxidation have been discussed with specific reference to the principle behind the expected synergism, different reactor configurations used and optimum considerations for the operating and geometric parameters. Some of the important works evaluating the application of these processes for the destruction of phenolic compounds has been described in details. Some guidelines for the future work required to facilitate efficient large-scale operation have also been given.

Compositional differences of phenolic compounds between black currant (Ribes nigrum L.) cultivars and their response to latitude and weather conditions.

PubMed

Zheng, Jie; Yang, Baoru; Ruusunen, Ville; Laaksonen, Oskar; Tahvonen, Risto; Hellsten, Jorma; Kallio, Heikki

2012-07-04

Phenolic compounds in black currants of three Finnish cultivars and their response to growth latitude and weather conditions were analyzed over a six-year period. 'Melalahti' had lower contents of total phenolic compounds (31.4% and 29.2% lower than 'Mortti' and 'Ola', respectively), total anthocyanins (32.6% and 30.5%), and total hydroxycinnamic acid derivatives (23.1% and 23.8%) (p < 0.05) and was less affected by growth latitude and weather conditions than 'Mortti' and 'Ola'. However, all the cultivars grown at higher latitude (66°34' N) had lower contents of total flavonols, total anthocyanins, and total phenolic compounds than those grown at lower latitude (60°23' N) (p < 0.05). The content of total hydroxycinnamic acid conjugates did not vary in 'Melalahti' (p > 0.05) but increased as the latitude increased in 'Mortti' and 'Ola' (p < 0.05). Temperature and radiation were the major weather variables influencing the composition of phenolic compounds. Delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, and myricetin-3-O-glucoside content showed positive correlations with temperature and radiation in all three cultivars. The study gives important guidelines for the selection of raw materials and growth sites as well as for the berry cultivation for commercial exploitation of black currant berries.

Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey.

PubMed

Estevinho, Letícia; Pereira, Ana Paula; Moreira, Leandro; Dias, Luís G; Pereira, Ermelinda

2008-12-01

Phenolic compounds of dark and clear honeys from Trás-os-Montes of Portugal were extracted with Amberlite XAD-2 and evaluated for their antioxidant and antimicrobial activities. The antioxidant effect was studied using the in vitro test capacity of scavenge the 2,2-diphenyl-1-picryhydrazyl (DPPH) free radical and of reducing power of iron (III)/ferricyanide complex. The antimicrobial activity was screened using three Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus, Staphylococcus lentus) and three Gram-negative bacteria (Pseudomonas aeruginosa, Klebsiella pneumoniae and Escherichia coli). The results obtained from the partial identification of honey phenolic compounds by high-performance liquid chromatography with a diode array detector showed that p-hydroxibenzoic acid, cinnamic acid, naringenin, pinocembrin and chrysin are the phenolic compounds present in most of the samples analyzed. Antioxidant potential was dependent of honey extract concentration and the results showed that dark honey phenolic compounds had higher activity than the obtained from clear honey. In the biological assays, results showed that S. aureus were the most sensitive microrganisms and B. subtilis, S. lentus, K. pneumoniae and E. coli were each moderately sensitive to the antimicrobial activity of honey extracts. Nevertheless, no antimicrobial activity was observed in the test with P. aeruginosa.

A general analytical strategy for the characterization of phenolic compounds in fruit juices by high-performance liquid chromatography with diode array detection coupled to electrospray ionization and triple quadrupole mass spectrometry.

PubMed

Abad-García, Beatriz; Berrueta, Luis A; Garmón-Lobato, Sergio; Gallo, Blanca; Vicente, Francisca

2009-07-10

In the present study, a methodology based on liquid chromatography with diode array detection (HPLC/DAD) coupled to an electrospray ionization (ESI) interface and a triple quadrupole mass spectrometer for the simultaneous identification of phenolic compounds in fruit juices has been developed. 72 available phenolic compound standards from diverse families present in fruits have been studied in order to analyze their fragmentation pattern. As a result, a general strategy for the characterization of unknown phenolic compounds in fruit juices was designed: (i) taking into account its UV-visible spectrum and elution order, assign the unknown polyphenol to a polyphenol class, (ii) identify the quasi-molecular ion using positive and negative MS spectra, being supported by adducts generated with solvent or sodium and molecular complexes, (iii) determinate the pattern of glycosylation in positive mode using ESI(+)-CID MS/MS product ion scan experiments, selecting the quasi-molecular ion as precursor ion, and finally, (iv) study the identity of the aglycone through ESI(+)-CID MS/MS product ion spectra from the protonated aglycone, [Y(0)](+). This strategy was successfully employed for the characterization of known and unknown phenolic compounds in juices from 17 different fruits.

Control of Maillard-type off-flavor development in ultrahigh-temperature-processed bovine milk by phenolic chemistry.

PubMed

Kokkinidou, Smaro; Peterson, Devin G

2014-08-13

The application of phenolic compounds to suppress Maillard chemistry and off-flavor development in ultrahigh-termperature (UHT)-processed milk during processing and storage was investigated. Five phenolic compounds were examined for structure-reactivity relationships (catechin, genistein, daidzein, 1,2,3-trihydroxybenzene, and 1,3,5-trihydroxybenzene). The levels of key transient Maillard reaction (MR) intermediates (reactive carbonyl species) and select off-flavor markers (methional, 2-acetyl-2-thiazoline, 2-acetyl-1-pyrroline) were quantified by LC-MS/MS and GC-MS/ToF, respectively. The addition of phenolic compounds prior to UHT processing significantly reduced the concentration of MR intermediates and related off-flavor compounds compared to a control sample (p < 0.05). All phenolic compounds demonstrated unique structure reactivity and, notably, those with a more activated A-ring for aromatic electrophilic substitution (catechin, genistein, and 1,3,5-trihydroxybenzene) showed the strongest suppression effect on the off-flavor markers and reactive carbonyl species. Sensory studies were in agreement with the analytical data. The cooked flavor intensity was rated lower for the recombination model samples of the catechin-treated UHT milk compared to the control UHT milk. Additionally, consumer acceptability studies showed catechin-treated UHT milk to have significantly higher liking scores when compared the control sample (Fisher's LSD = 0.728).

Effects of copper on the antioxidant activity of olive polyphenols in bulk oil and oil-in-water emulsions.

PubMed

Paiva-Martins, Fátima; Santos, Vera; Mangericão, Hugo; Gordon, Michael H

2006-05-17

The antioxidant activity and interactions with copper of four olive oil phenolic compounds, namely oleuropein, hydroxytyrosol, 3,4-dihydroxyphenylethanol-elenolic acid (1), and 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde (2), in olive oil and oil-in-water emulsions stored at 60 degrees C were studied. All four phenolic compounds significantly extended the induction time of lipid oxidation in olive oil with the order of activity being hydroxytyrosol > compound 1 > compound 2 > oleuropein > alpha-tocopherol; but in the presence of Cu(ll), the stability of oil samples containing phenolic compounds decreased by at least 90%, and the antioxidant activity of hydroxytyrosol and compounds 1 and 2 became similar. In oil-in-water emulsions prepared from olive oil stripped of tocopherols, hydroxytyrosol enhanced the prooxidant effect of copper at pH 5.5 but not at pH 7.4. The stability of samples containing copper at pH 5.5 was not significantly different if oleuropein was present from that of the control. Oleuropein at pH 7.4, and compounds 1 and 2 at both pH values tested, reduced the prooxidant effect of copper. The lower stability and the higher reducing capacity of all compounds at pH 7.4 could not explain the higher stability of emulsions containing phenolic compounds at this pH value. However, mixtures containing hydroxytyrosol or oleuropein with copper showed higher 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity at pH 7.4 than at pH 5.5. Moreover, the compound 2-copper complex showed higher radical scavenging activity then the uncomplexed compound at pH 5.5. It can be concluded that the formation of a copper complex with radical scavenging activity is a key step in the antioxidant action of the olive oil phenolic compounds in an emulsion containing copper ions.

Impact of bioaccessibility and bioavailability of phenolic compounds in biological systems upon the antioxidant activity of the ethanolic extract of Triplaris gardneriana seeds.

PubMed

Neto, José Joaquim Lopes; de Almeida, Thiago Silva; de Medeiros, Jackeline Lima; Vieira, Leonardo Rogério; Moreira, Thaís Borges; Maia, Ana Isabel Vitorino; Ribeiro, Paulo Riceli Vasconcelos; de Brito, Edy Sousa; Farias, Davi Felipe; Carvalho, Ana Fontenele Urano

2017-04-01

The most studied bioactive potential of phenolic compounds corresponds to antioxidant activity, which in turn, is associated with a reduction in the incidence of various human diseases. However, the total quantity of these bioactive substances in foods and medicinal preparations does not reflect the amount absorbed and metabolized by the body. The present study aimed to investigate the bioaccessibility of Triplaris gardneriana seeds ethanolic extract (EETg) by determination of phenolic composition and antioxidant activities before and after in vitro digestion as well as to estimate its bioavailability by chemical analysis of plasma and urine in animal models after oral administration. The bioaccessibility indexes of phenolic compounds in EETg were 48.65 and 69.28% in the presence and absence of enzymes, respectively. Among the identified phenolics classes, flavonoids, represented by galloylated procyanidins type B, proved to be more bioaccessible, 81.48 and 96.29% in the post-intestinal phase with and without enzymes, respectively. The oral administration in Wistar rats resulted in a significant decrease in plasma of the total antioxidant capacity, TAC, by FRAP assay 4h after beginning the experiment. For urine samples, an increase in TAC by DPPH and FRAP was observed from 1 and 4h after administration, respectively. UPLC-QTOF analysis of urine detected 2 metabolites originated from the degradation of phenolic compounds, i.e. hippuric acid and phenylacetil glycine. These results suggest that phenolic compounds in T. gardneriana are unstable under gastrointestinal conditions, being flavonoids the components with higher bioaccessibility; besides that, they showed limited bioavailability due to their rapid biotransformation and urinary elimination. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Phenolic compounds of Pinus laricio needles: a bioindicator of the effects of prescribed burning in function of season.

PubMed

Cannac, Magali; Pasqualini, Vanina; Barboni, Toussaint; Morandini, Frederic; Ferrat, Lila

2009-07-15

Fire is a dominant ecological factor in Mediterranean-type ecosystems. Forest management includes many preventive tools, in particular for fire prevention, such as mechanical treatments and prescribed burning. Prescribed burning is a commonly used method for treating fuel loads, but fuel reduction targets for reducing wildfire hazards must be balanced against fuel retention targets in order to maintain habitat and other forest functions. This approach was used on Pinus nigra ssp laricio var. Corsicana, a pine endemic to Corsica of great ecological and economic importance. Many studies of plant phenolic compounds have been carried out concerning responses to various stresses. The aim of this study was to understand i) the effects of prescribed burning 1 to 16 months later and ii) the effects of the seasonality of burning, spring or fall, on the production of phenolic compounds in Pinus laricio. After prescribed burning conducted in spring, Pinus laricio increases the synthesis of total phenolic compounds for a period of 7 months. The increase is greater after spring-burning than fall-burning. With regard to simple phenols, only dihydroferulic acid responds about 1 year after both types of prescribed burning. The causes of these increases are discussed in this paper. Total phenolic compounds could be used as a bioindicator for the short-term response of Pinus laricio needles to prescribed burning. Simple phenols may be useful for revealing the medium-term effects of prescribed burning. The results of this study include recommending forest managers to use prescribed burning in the fall rather than spring to reduce fuel loads and have less impact on the trees.

Phylogenetic and functional diversity of metagenomic libraries of phenol degrading sludge from petroleum refinery wastewater treatment system

PubMed Central

2012-01-01

In petrochemical refinery wastewater treatment plants (WWTP), different concentrations of pollutant compounds are received daily in the influent stream, including significant amounts of phenolic compounds, creating propitious conditions for the development of particular microorganisms that can rapidly adapt to such environment. In the present work, the microbial sludge from a refinery WWTP was enriched for phenol, cloned into fosmid vectors and pyrosequenced. The fosmid libraries yielded 13,200 clones and a comprehensive bioinformatic analysis of the sequence data set revealed a complex and diverse bacterial community in the phenol degrading sludge. The phylogenetic analyses using MEGAN in combination with RDP classifier showed a massive predominance of Proteobacteria, represented mostly by the genera Diaphorobacter, Pseudomonas, Thauera and Comamonas. The functional classification of phenol degrading sludge sequence data set generated by MG-RAST showed the wide metabolic diversity of the microbial sludge, with a high percentage of genes involved in the aerobic and anaerobic degradation of phenol and derivatives. In addition, genes related to the metabolism of many other organic and xenobiotic compounds, such as toluene, biphenyl, naphthalene and benzoate, were found. Results gathered herein demonstrated that the phenol degrading sludge has complex phylogenetic and functional diversities, showing the potential of such community to degrade several pollutant compounds. This microbiota is likely to represent a rich resource of versatile and unknown enzymes which may be exploited for biotechnological processes such as bioremediation. PMID:22452812

The effect of drying temperatures on antioxidant activity, phenolic compounds, fatty acid composition and tocopherol contents in citrus seed and oils.

PubMed

Al Juhaimi, Fahad; Özcan, Mehmet Musa; Uslu, Nurhan; Ghafoor, Kashif

2018-01-01

In this study, the effect of drying temperature on antioxidant activity, phenolic compounds, fatty acid composition and tocopherol content of citrus seeds and oils were studied. Kinnow mandarin seed, dried at 60 °C, exhibited the highest antioxidant activity. Orlendo orange seed had the maximum total phenolic content and α-tocopherol content, with a value of 63.349 mg/100 g and 28.085 mg/g (control samples), respectively. The antioxidant activity of Orlendo orange seed (63.349%) was higher than seeds of Eureka lemon (55.819%) and Kinnow mandarin (28.015%), while the highest total phenolic content was found in seeds of Kinnow mandarin, followed by Orlendo orange and Eureka lemon (113.132). 1.2-Dihydroxybenzene (13.171), kaempferol (10.780), (+)-catechin (9.341) and isorhamnetin (7.592) in mg/100 g were the major phenolic compounds found in Kinnow mandarin. Among the unsaturated fatty acids, linoleic acid was the most abundant acid in all oils, which varied from 44.4% (dried at 80 °C) to 46.1% (dried at 70 °C), from 39.0% (dried at 60 °C) to 40.0% (dried at 70 °C). The total phenolic content, antioxidant activity and phenolic compounds of citrus seeds and tocopherol content of seed oils were significantly affected by drying process and varied depending on the drying temperature.

Solid state fermentation of Trichoderma viride for enhancement phenolic content, antioxidant and antimicrobial activities in ginger.

PubMed

Saleh, Rashad M; Kabli, Saleh A; Al-Garni, Saleh M; Al-Ghamdi, Maryam A; Abdel-Aty, Azza M; Mohamed, Saleh A

2018-05-04

The phenolic content of methanolic and water extracts of ginger fermented by Trichoderma spp. during solid state fermentation (SSF) was detected as compared with unfermented ginger. The total phenolic content of fermented ginger increased several times. The highest phenolic content of ginger was detected after SSF by T. viride. The optimal physiological conditions for the maximum production of the phenolic content and β-glucosidase activity of fermented ginger by T. viride were detected at day 7 incubation, pH 6.0, 30°C and 30% moisture. There are consistent between the maximum production of β-glucosidase and phenolic content. The SSF of ginger by T. viride greatly enhanced the antioxidant potency of phenolic compounds by using DPPH and ABTS assays. Potent antibacterial activity was appeared by phenolic compounds of fermented ginger against all the tested human-pathogenic bacteria. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

A new phenol glycoside from Physalis angulata.

PubMed

Sun, Cheng-Peng; Nie, Xiu-Fang; Kang, Ning; Zhao, Feng; Chen, Li-Xia; Qiu, Feng

2017-05-01

A new phenol glycoside, physanguloside A (1), was isolated from Physalis angulata together with four known compounds. We report herein, for the first time, the presence of compounds 2-5 in the genus Physalis. The structures of all the compounds were established by NMR, IR, UV and HRESIMS spectroscopic analyses, and comparison with the literature data. All isolated compounds were assayed for inhibitory activity on nitric oxide production by LPS-induced in RAW 264.7 macrophages.

Natural mediators in the oxidation of polycyclic aromatic hydrocarbons by laccase mediator systems

DOE Office of Scientific and Technical Information (OSTI.GOV)

Johannes, C.; Majcherczyk, A.

2000-02-01

The oxidation of polycyclic aromatic compounds was studied in systems consisting of laccase from Trametes versicolor and so-called mediator compounds. The enzymatic oxidation of acenaphthene, acenaphthylene, anthracene, and fluorene was mediated by various laccase substrates (phenols and aromatic amines) or compounds produced and secreted by white rot fungi. The best natural mediators, such as phenol, aniline, 4-hydroxybenzoic acid, and 4-hydroxybenzyl alcohol were as efficient as the previously described synthetic compounds ABTS [2,2{prime}-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid)] and 1-hydroxybenzotriazole. The oxidation efficiency increased proportionally with the redox potentials of the phenolic mediators up to a maximum value of 0.9 V and decreased thereafter withmore » redox potentials exceeding this value. Natural compounds such as methionine, cysteine, and reduced glutathione, containing sulfhydryl groups, were also active as mediator compounds.« less

Phenolic glycosides and ionone glycoside from the stem of Sargentodoxa cuneata.

PubMed

Chang, Jun; Case, Ryan

2005-12-01

Four phenolic glycosides, cuneatasides A-D (1-4), and one ionone glycoside cuneataside E (5), together with seven known phenolic compounds (6-12) were isolated from the water-soluble constituents of the stem of Sargentodoxa cuneata (Sargentodoxaceae). Their structures were elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed compounds 1 and 2 to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus epidermidis.

Radionuclide-binding compound, a radionuclide delivery system, a method of making a radium complexing compound, a method of extracting a radionuclide, and a method of delivering a radionuclide

DOEpatents

Fisher, Darrell R.; Wai, Chien M.; Chen, Xiaoyuan

2000-01-01

The invention pertains to compounds which specifically bind radionuclides, and to methods of making radionuclide complexing compounds. In one aspect, the invention includes a radionuclide delivery system comprising: a) a calix[n]arene-crown-[m]-ether compound, wherein n is an integer greater than 3, and wherein m is an integer greater than 3, the calix[n]arene-crown-[m]-ether compound comprising at least two ionizable groups; and b) an antibody attached to the calix[n]arene-crown-[m]-ether compound. In another aspect, the invention includes a method of making a radium complexing compound, comprising: a) providing a calix[n]arene compound, wherein n is an integer greater than 3, the calix[n]arene compound comprising n phenolic hydroxyl groups; b) providing a crown ether precursor, the crown ether precursor comprising a pair of tosylated ends; c) reacting the pair of tosylated ends with a pair of the phenolic hydroxyl groups to convert said pair of phenolic hydroxyl groups to ether linkages, the ether linkages connecting the crown ether precursor to the calix[n]arene to form a calix[n]arene-crown-[m]-ether compound, wherein m is an integer greater than 3; d) converting remaining phenolic hydroxyl groups to esters; e) converting the esters to acids, the acids being proximate a crown-[m]-ether portion of the calix[n]arene-crown-[m]-ether compound; and f) providing a Ra.sup.2+ ion within the crown-[m]-ether portion of the calix[n]arene-crown-[m]-ether compound.

Phenolic plant metabolites as bioactive food and feed additives

USDA-ARS?s Scientific Manuscript database

Functional additives in food and animal feed formulations are gaining acceptance as consumers and producers recognize the health benefits associated with certain natural plant products. Phenolic compounds in particular have emerged as a class of compounds with antioxidant, antibacterial, and antifun...

Analysis of phenolic compounds extracted from peanut seed testa

USDA-ARS?s Scientific Manuscript database

Peanuts (Arachis hypogaea) contain numerous phenolic compounds with antimicrobial and antioxidant properties. These secondary metabolites may be isolated as co-products from peanut skins or testae during peanut processing and have potential use in functional food or feed formulations. Peanut skins w...

Bioactive compounds and antioxidant capacity of extruded snack-type products developed from novel formulations of lentil and nutritional yeast flours.

PubMed

Ciudad-Mulero, María; Barros, Lillian; Fernandes, Ângela; Berrios, José De J; Cámara, Montaña; Morales, Patricia; Fernández-Ruiz, Virginia; Ferreira, Isabel C F R

2018-02-21

Pulses are well known to be gluten-free functional foods that provide a rich source of nutritional and healthy compounds with antioxidant-promoting activity. In the present study, the bioactive compounds, dietary fibre, arabinoxylans, individual phenolic compounds and tocopherols, were evaluated in different lentil flours (raw and extruded at 140 and 160 °C) formulated with nutritional yeasts, along with the changes induced by the extrusion process. The total dietary fibre and arabinoxylan content significantly (p < 0.05) increased after the extrusion process while a significant decrease of all tocopherol isoforms was also observed. Catechin, caffeic, kaempferol and quercetin derivatives were identified in the raw and extruded lentil flours. The decreases of total phenolic and individual phenolic compounds were directly related to the extrusion temperature; total phenolics and catechin hexoside exhibited a larger decrease in the lentil flours formulated with higher content of nutritional yeast (12 and 16%). The antioxidant activity results, determined using different assays, reflected the important effect of extrusion processing and food ingredients.

Naked eye screening of 11 phenolic compounds and colorimetric determination using polydiacetylene vesicles with α-cyclodextrin

NASA Astrophysics Data System (ADS)

Anekthirakun, Pimpimon; Sukwattanasinitt, Mongkol; Tuntulani, Thawatchai; Imyim, Apichat

2013-07-01

The colorimetric response (CR) of poly(10,12-pentacosadiynoic acid) vesicles (PPCDA) induced by α-cyclodextrin (α-CD) in an aqueous solution has been studied. Various parameters affecting the CR, such as response time and concentration were investigated. The blue color of 0.01 mM PPCDA solution became pinkish red with the addition of α-CD at the concentration higher than 3 mM. The inhibition of the color transition from blue to red was investigated using 11 phenolic compounds. The color transition could be inhibited and observed by naked eye in the presence of 4 phenolic compounds, i.e. 4-nitrophenol (4-NP) and 4-bromophenol (4-BP) and 4-chlorophenol (4-CP) and 3-nitrophenol (3-NP). A colorimetric method for the determination of these compounds was validated and applied for surface water analysis. The linear range from the plot of CR against phenolic compounds concentration was in the order of 0.5-2.0 mM with R2 more than 0.99. The recoveries were 90-95% with good precision (1-4%RSD, n = 10).

Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.

PubMed

Sinha, Arun Kumar; Verma, Subash Chandra; Sharma, Upendra Kumar

2007-01-01

A simple and fast method was developed using RP-HPLC for separation and quantitative determination of vanillin and related phenolic compounds in ethanolic extract of pods of Vanilla planifolia. Ten phenolic compounds, namely 4-hydroxybenzyl alcohol, vanillyl alcohol, 3,4-dihydroxybenzaldehyde, 4-hydroxybenzoic acid, vanillic acid, 4-hydroxybenzaldehyde, vanillin, p-coumaric acid, ferulic acid, and piperonal were quantitatively determined using ACN, methanol, and 0.2% acetic acid in water as a mobile phase with a gradient elution mode. The method showed good linearity, high precision, and good recovery of compounds of interest. The present method would be useful for analytical research and for routine analysis of vanilla extracts for their quality control.

Quenching of fluorescence of phenolic compounds and modified humic acids by cadmium ions.

PubMed

Tchaikovskaya, O N; Nechaev, L V; Yudina, N V; Mal'tseva, E V

2016-08-01

The interaction of a number of phenolic compounds, being 'model fragments' of humic acids, with cadmium ions was investigated. The fluorescence quenching method was used to determine the complexation constants of these compounds with cadmium ions. It was established that bonding of phenolic compounds by cadmium ions at рН 7 is weak and reaches a maximum value of 15% for interaction with resorcinol. It was demonstrated that modification of humic acids by the mechanoactivation method increases by three times bonding of cadmium ions, which is caused by strengthening the acid properties of carboxyl and hydroxyl groups at the aromatic ring. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

Analysis of phenolic choline esters from seeds of Arabidopsis thaliana and Brassica napus by capillary liquid chromatography/electrospray- tandem mass spectrometry.

PubMed

Böttcher, Christoph; von Roepenack-Lahaye, Edda; Schmidt, Jürgen; Clemens, Stephan; Scheel, Dierk

2009-04-01

Total phenolic choline ester fractions prepared from seeds of Arabidopsis thaliana and Brassica napus were analyzed by capillary LC/ESI-QTOF-MS and direct infusion ESI-FTICR-MS. In addition to the dominating sinapoylcholine, 30 phenolic choline esters could be identified based on accurate mass measurements, interpretation of collision-induced dissociation (CID) mass spectra, and synthesis of selected representatives. The compounds identified so far include substituted hydroxycinnamoyl- and hydroxybenzoylcholines, respective monohexosides as well as oxidative coupling products of phenolic choline esters and monolignols. Phenolic choline esters are well separable by reversed-phase liquid chromatography and sensitively detectable using electrospray ionization mass spectrometry in positive ion mode. CID mass spectra obtained from molecular ions facilitate the characterization of both the type and substitution pattern of such compounds. Therefore, LC/ESI-MS/MS represents a valuable tool for comprehensive qualitative and quantitative analysis of this compound class. Copyright (c) 2009 John Wiley & Sons, Ltd.

Phenolic profile, antioxidant activity and palynological analysis of stingless bee honey from Amazonas, Northern Brazil.

PubMed

da Silva, Isnandia Andréa Almeida; da Silva, Tania Maria Sarmento; Camara, Celso Amorim; Queiroz, Neide; Magnani, Marciane; de Novais, Jaílson Santos; Soledade, Luiz Edmundo Bastos; Lima, Edeltrudes de Oliveira; de Souza, Antonia Lucia; de Souza, Antonio Gouveia

2013-12-15

In this study honey samples produced by Melipona (Michmelia) seminigra merrillae, collected in seven counties distributed in the central and southern region of Amazonas state in Brazil, were analysed for their botanical origin, content and profile of phenolic compounds, and antioxidant and antimicrobial activities. Twenty-two pollen types were identified. The total phenolic content ranged from 17 to 66 mg GAE/g of extract; the highest contents were found in honeys produced from pollen types such as Clidemia and Myrcia. The antioxidant activity was higher in the samples that contained higher quantities of phenolic compounds. In relation to the antibacterial activity, samples CAD3, CAD4 and SAD3 presented the best results. Fourteen phenolic compounds were determined. Among them, we identified the flavonoid taxifolin, which has not previously been described in honeys from stingless bees, and we report the identification of catechol in Brazilian honey samples for the first time. Copyright © 2013 Elsevier Ltd. All rights reserved.

Profiling of Phenolic Compounds and Antioxidant Activity of 12 Cruciferous Vegetables.

PubMed

Li, Zhifeng; Lee, Hui Wen; Liang, Xu; Liang, Dong; Wang, Qi; Huang, Dejian; Ong, Choon Nam

2018-05-10

The phenolic profiles of 12 cruciferous vegetables (pakchoi, choysum, Chinese cabbage, kailan, Brussels sprout, cabbage, cauliflower, broccoli, rocket salad, red cherry radish, daikon radish, and watercress) were studied with UHPLC-MS/MS. Antioxidant activity and total phenolic content (TPC) were also evaluated. A total of 74 phenolic compounds were identified, including 16 hydroxycinnamic acids and derivatives, and 58 flavonoids and derivatives. The main flavonoids identified were glycosylated quercetin, kaempferol and isorhamnetin, and the main hydroxycinnamic acids were ferulic, sinapic, caffeic and p -coumaric acids. Principal component analysis (PCA) revealed that the distribution of phenolic compounds in different genera of cruciferous vegetables was in accordance with their conventional taxonomy. The DPPH, ORAC and TPC values ranged from 1.11 to 9.54 µmoles Trolox equivalent/g FW, 5.34 to 32.92 µmoles Trolox equivalent/g FW, and 0.16 to 1.93 mg gallic acid equivalent/g FW respectively. Spearman’s correlation showed significant ( p < 0.05) positive correlations between TPC, flavonoids and antioxidant activity.

Assessment of the antioxidant and antibacterial activities of different olive processing wastewaters

PubMed Central

Tan, Shiau Pin; El-Abbassi, Abdelilah; Kiai, Hajar; Hafidi, Abdellatif; O’Donovan, Orla; McLoughlin, Peter

2017-01-01

Olive processing wastewaters (OPW), namely olive mill wastewater (OMW) and table-olive wastewaters (TOW) were evaluated for their antibacterial activity against five Gram-positive and two Gram-negative bacteria using the standard disc diffusion and thin layer chromatography (TLC)-bioautography assays. Disc diffusion screening and bioautography of OMW were compared to the phenolic extracts of table-olive brines. Positive activity against S. aureus was demonstrated. The optimization of chromatographic separation revealed that hexane/acetone in the ratio of 4:6 was the most effective for phenolic compounds separation. A HPLC-MS analysis was performed showing that only two compounds, hydroxytyrosol and tyrosol, were the predominant phenolic compounds in all OPW. The phenolic extract of OMW generated by a semi-modern process showed the highest free radical-scavenging activity (DPPH assay) compared to the other phenolic extracts. It is apparent from the present study that OPW are a rich source of antioxidants suitable for use in food, cosmetic or pharmaceutical applications. PMID:28873097

Phenolic profile and antioxidant activity from non-toxic Mexican Jatropha curcas L. shell methanolic extracts.

PubMed

Perea-Domínguez, Xiomara Patricia; Espinosa-Alonso, Laura Gabriela; Hosseinian, Farah; HadiNezhad, Mehri; Valdez-Morales, Maribel; Medina-Godoy, Sergio

2017-03-01

Jatropha curcas seed shells are the by-product obtained during oil extraction process. Recently, its chemical composition has gained attention since its potential applications. The aim of this study was to identify phenolic compounds profile from a non-toxic J. curcas shell from Mexico, besides, evaluate J. curcas shell methanolic extract (JcSME) antioxidant activity. Free, conjugate and bound phenolics were fractionated and quantified (606.7, 193.32 and 909.59 μg/g shell, respectively) and 13 individual phenolic compounds were detected by HPLC. The radical-scavenging activity of JcSME was similar to Trolox and ascorbic acid by DPPH assay while by ABTS assay it was similar to BHT. Effective antioxidant capacity by ORAC was found (426.44 ± 53.39 μmol Trolox equivalents/g shell). The Mexican non-toxic J. curcas shell is rich in phenolic compounds with high antioxidant activity; hence, it could be considerate as a good source of natural antioxidants.

Substituent effect of phenolic aldehyde inhibition on alcoholic fermentation by Saccharomyces cerevisiae

Treesearch

Rui Xie; Maobing Tu; Thomas Elder

2016-01-01

Phenolic compounds significantly inhibit microbial fermentation of biomass hydrolysates. To understand thequantitative structure-inhibition relationship of phenolic aldehydes on alcoholic fermentation, the effect of 11 differentsubstituted benzaldehydes on the final ethanol yield was examined. The results showed that the degree of phenolic...

Phenolic content and antioxidant capacity in algal food products.

PubMed

Machu, Ludmila; Misurcova, Ladislava; Ambrozova, Jarmila Vavra; Orsavova, Jana; Mlcek, Jiri; Sochor, Jiri; Jurikova, Tunde

2015-01-12

The study objective was to investigate total phenolic content using Folin-Ciocalteu's method, to assess nine phenols by HPLC, to determine antioxidant capacity of the water soluble compounds (ACW) by a photochemiluminescence method, and to calculate the correlation coefficients in commercial algal food products from brown (Laminaria japonica, Eisenia bicyclis, Hizikia fusiformis, Undaria pinnatifida) and red (Porphyra tenera, Palmaria palmata) seaweed, green freshwater algae (Chlorella pyrenoidosa), and cyanobacteria (Spirulina platensis). HPLC analysis showed that the most abundant phenolic compound was epicatechin. From spectrophotometry and ACW determination it was evident that brown seaweed Eisenia bicyclis was the sample with the highest phenolic and ACW values (193 mg·g-1 GAE; 7.53 µmol AA·g-1, respectively). A linear relationship existed between ACW and phenolic contents (r = 0.99). Some algal products seem to be promising functional foods rich in polyphenols.

In-Depth Two-Year Study of Phenolic Profile Variability among Olive Oils from Autochthonous and Mediterranean Varieties in Morocco, as Revealed by a LC-MS Chemometric Profiling Approach.

PubMed

Bajoub, Aadil; Medina-Rodríguez, Santiago; Olmo-García, Lucía; Ajal, El Amine; Monasterio, Romina P; Hanine, Hafida; Fernández-Gutiérrez, Alberto; Carrasco-Pancorbo, Alegría

2016-12-28

Olive oil phenolic fraction considerably contributes to the sensory quality and nutritional value of this foodstuff. Herein, the phenolic fraction of 203 olive oil samples extracted from fruits of four autochthonous Moroccan cultivars ("Picholine Marocaine", "Dahbia", "Haouzia" and "Menara"), and nine Mediterranean varieties recently introduced in Morocco ("Arbequina", "Arbosana", "Cornicabra", "Frantoio", "Hojiblanca", "Koroneiki", "Manzanilla", "Picholine de Languedoc" and "Picual"), were explored over two consecutive crop seasons (2012/2013 and 2013/2014) by using liquid chromatography-mass spectrometry. A total of 32 phenolic compounds (and quinic acid), belonging to five chemical classes (secoiridoids, simple phenols, flavonoids, lignans and phenolic acids) were identified and quantified. Phenolic profiling revealed that the determined phenolic compounds showed variety-dependent levels, being, at the same time, significantly affected by the crop season. Moreover, based on the obtained phenolic composition and chemometric linear discriminant analysis, statistical models were obtained allowing a very satisfactory classification and prediction of the varietal origin of the studied oils.

Molecularly imprinted solid-phase extraction combined with high performance liquid chromatography for analysis of phenolic compounds from environmental water samples.

PubMed

Feng, Qin-Zhong; Zhao, Li-Xia; Yan, Wei; Lin, Jin-Ming; Zheng, Zhi-Xia

2009-08-15

The molecularly imprinted bulk polymer with 2,4,6-trichlorophenol (2,4,6-TCP) as the template molecule and methylacrylic acid (MAA), ethylene glycol dimethacrylate (EGDMA) as functional monomer and the crosslinker, respectively, has been prepared and applied to the molecularly imprinted solid-phase extraction (MISPE) procedure for selective preconcentration of phenolic compounds from environmental water samples. Various parameters affecting the extraction efficiency of the polymer have been evaluated to optimize the selective preconcentration of the phenolic compounds from aqueous samples. The characteristics of the MISPE method were validated by HPLC. The recoveries ranged between 90% and 98% (RSD: 0.9-2.3%, n=3) for tap water, between 85% and 105% (RSD: 2.6-4.9%, n=3) for river water, between 78% and 98% (RSD: 2.6-5.4%, n=3) for sewage water fortified with 0.4 mg L(-1) of phenol, 4-chlorophenol (4-CP), 2,4-dichlorophenol (2,4-DCP), pentachlorophenol (PCP). It was demonstrated that this MISPE-HPLC method could be applied to direct preconcentration and determination of phenolic compounds in environmental water samples.

Mixture Design and Doehlert Matrix for the Optimization of the Extraction of Phenolic Compounds from Spondias mombin L Apple Bagasse Agroindustrial Residues.

PubMed

Santos Felix, Antonio C; Novaes, Cleber G; Pires Rocha, Maísla; Barreto, George E; do Nascimento, Baraquizio B; Giraldez Alvarez, Lisandro D

2017-01-01

In this study, we have determined, using RSM (mixture design and Doehlert matrix), the optimum values of the independent variables to achieve the maximum response for the extraction of total phenolic compounds from Spondias mombin L bagasse agroindustrial residues in order to preserve their antioxidant activity. The extraction of phenolic compounds, as well as their antioxidant capacity and the capacity to scavenge ABTS, was determined by the modified DPPH method at different periods of time, temperature, velocity of rotation and solvents concentration. We observed that the optimum condition for the highest antioxidant yield was obtained using water (60.84%), acetone (30.31%), and ethanol (8.85%) at 30°C during 20 min at 50 rpm. We have also found that the maximum yield of total phenolics was 355.63 ± 9.77 (mg GAE/100 g), showing an EC 50 of 3,962.24 ± 41.20 (g fruit/g of DPPH) and 8.36 ± 0.30 (μM trolox/g fruit), which were measured using DPPH and ABTS assays. These results suggest that RSM was successfully applied for optimizing the extraction of phenolics compounds thus preserving their antioxidant activity.

Ultrasound-assisted extraction of bioactive compounds from lemon balm and peppermint leaves

NASA Astrophysics Data System (ADS)

Šic Žlabur, Jana; Voća, Sandra; Dobričević, Nadica; Pliestić, Stjepan; Galić, Ante; Boričević, Ana; Borić, Nataša

2016-01-01

The aim of this study was to investigate the influence of conventional and ultrasound-assisted extraction (frequency, time, temperature) on the content of bioactive compounds as well as on the antioxidant activity of aqueous extracts from fresh lemon balm and peppermint leaves. Total phenols, flavonoids, non-flavonoids, total chlorophylls, total carotenoids, and radical scavenging capacity were determined. Moreover, the relationship between bioactive compounds and antioxidant capacity was studied by linear regression. A significant increase in all studied bioactive compounds during ultrasonic extraction for 5 to 20 min was found. With the classical extraction method, the highest amounts of total phenols, flavonoids, and antioxidant activity were determined, and the maximum amounts of total chlorophylls and carotenoids were determined during 20 min ultrasonic extraction. The correlation analysis revealed a strong, positive relationship between antioxidant activity and total phenolic compounds.

Identification of phenolic compounds in red wine extract samples and zebrafish embryos by HPLC-ESI-LTQ-Orbitrap-MS.

PubMed

Vallverdú-Queralt, Anna; Boix, Nuria; Piqué, Ester; Gómez-Catalan, Jesús; Medina-Remon, Alexander; Sasot, Gemma; Mercader-Martí, Mercè; Llobet, Juan M; Lamuela-Raventos, Rosa M

2015-08-15

The zebrafish embryo is a highly interesting biological model with applications in different scientific fields, such as biomedicine, pharmacology and toxicology. In this study, we used liquid chromatography/electrospray ionisation-linear ion trap quadrupole-Orbitrap-mass spectrometry (HPLC/ESI-LTQ-Orbitrap-MS) to identify the polyphenol compounds in a red wine extract and zebrafish embryos. Phenolic compounds and anthocyanin metabolites were determined in zebrafish embryos previously exposed to the red wine extract. Compounds were identified by injection in a high-resolution system (LTQ-Orbitrap) using accurate mass measurements in MS, MS(2) and MS(3) modes. To our knowledge, this research constitutes the first comprehensive identification of phenolic compounds in zebrafish by HPLC coupled to high-resolution mass spectrometry. Copyright © 2015 Elsevier Ltd. All rights reserved.

Determination of phenolic priority pollutants utilizing permeation sampling method

DOE Office of Scientific and Technical Information (OSTI.GOV)

Zhang, Guozheng.

1990-01-01

A passive permeation sampling method for the determination of phenolic priority pollutants in water was developed. Phenols in an aqueous solution permeate a polymeric membrane and are collected on a solid adsorbent in a sampling device. Both solvent and thermal desorption techniques were employed to recovery phenolic pollutants collected. In the solvent desorption, phenolic compounds collected on the XAD-7 resin, and then desorbed by acetonitrile. In the thermal desorption, phenolic compounds collected on Tenax-TA were recovered thermally, Separation and quantification is achieved by a SPB-5 capillary column gas chromatography using a flame ionization detector. There are linear relationships between themore » amount of phenolic compounds collected and the products of the exposure times and concentrations over the range from 5 ppb to 20 ppm with precisions no worse than 13%. The permeation rates of the phenolic pollutants depend upon the exposure temperature, solution pH and membrane area. Samples collected can be stored for up to two weeks without loss. This method provides a simple, convenient and inexpensive way for monitoring the time-weighted-average concentration without the use of a pumping system. An automated sampler which combines the permeation and the thermal desorption techniques together was also developed for water sample obtained from grab sampling. The on-line setup provides a high degree of automation. Detection limits at 10 ppb can be achieved using this sampler.« less

Alkaline extraction of phenolic compounds from intact sorghum kernels

USDA-ARS?s Scientific Manuscript database

An aqueous sodium hydroxide solution was employed to extract phenolic compounds from whole grain sorghum without decortication or grinding as determined by Oxygen Radical Absorbance Capacity (ORAC). The alkaline extract ORAC values were more stable over 32 days compared to neutralized and freeze dri...

Nondestructive application of laser-induced fluorescence spectroscopy for quantitative analyses of phenolic compounds in strawberry fruits (Fragaria x ananassa).

PubMed

Wulf, J S; Rühmann, S; Rego, I; Puhl, I; Treutter, D; Zude, M

2008-05-14

Laser-induced fluorescence spectroscopy (LIFS) was nondestructively applied on strawberries (EX = 337 nm, EM = 400-820 nm) to test the feasibility of quantitatively determining native phenolic compounds in strawberries. Eighteen phenolic compounds were identified in fruit skin by UV and MS spectroscopy and quantitatively determined by use of rp-HPLC for separation and diode-array or chemical reaction detection. Partial least-squares calibration models were built for single phenolic compounds by means of nondestructively recorded fluorescence spectra in the blue-green wavelength range using different data preprocessing methods. The direct orthogonal signal correction resulted in r (2) = 0.99 and rmsep < 8% for p-coumaroyl-glucose, and r (2) = 0.99 and rmsep < 24% for cinnamoyl-glucose. In comparison, the correction of the fluorescence spectral data with simultaneously recorded reflectance spectra did not further improve the calibration models. Results show the potential of LIFS for a rapid and nondestructive assessment of contents of p-coumaroyl-glucose and cinnamoyl-glucose in strawberry fruits.

Evaluation of phenolic compounds in maté ( Ilex paraguariensis) processed by gamma radiation

NASA Astrophysics Data System (ADS)

Furgeri, C.; Nunes, T. C. F.; Fanaro, G. B.; Souza, M. F. F.; Bastos, D. H. M.; Villavicencio, A. L. C. H.

2009-07-01

The radiation food processing has been demonstrating great effectiveness in the attack of pathogenic agents, while little compromising nutritional value and sensorial properties of foods. The maté ( Ilex paraguariensis), widely consumed product in South America, generally in the form of infusions with hot or cold water, calls of chimarrão or tererê, it is cited in literature as one of the best sources phenolic compounds. The antioxidants action of these constituent has been related to the protection of the organism against the free radicals, generated in alive, currently responsible for the sprouting of some degenerative illness as cancer, arteriosclerosis, rheumatic arthritis and cardiovascular clutters among others. The objective of that work was to evaluate the action of the processing for gamma radiation in phenolic compounds of tererê beverage in the doses of 0, 3, 5, 7 and 10 kGy. The observed results do not demonstrate significant alterations in phenolic compounds of tererê beverage processed by gamma radiation.

Removal of furan and phenolic compounds from simulated biomass hydrolysates by batch adsorption and continuous fixed-bed column adsorption methods.

PubMed

Lee, Sang Cheol; Park, Sunkyu

2016-09-01

It has been proposed to remove all potential inhibitors and sulfuric acid in biomass hydrolysates generated from dilute-acid pretreatment of biomass, based on three steps of sugar purification process. This study focused on its first step in which furan and phenolic compounds were selectively removed from the simulated hydrolysates using activated charcoal. Batch adsorption experiments demonstrated that the affinity of activated charcoal for each component was highest in the order of vanillic acid, 4-hydroxybenzoic acid, furfural, acetic acid, sulfuric acid, and xylose. The affinity of activated charcoal for furan and phenolic compounds proved to be significantly higher than that of the other three components. Four separation strategies were conducted with a combination of batch adsorption and continuous fixed-bed column adsorption methods. It was observed that xylose loss was negligible with near complete removal of furan and phenolic compounds, when at least one fixed-bed column adsorption was implemented in the strategy. Copyright © 2016 Elsevier Ltd. All rights reserved.

Optimization of ultrasound-assisted extraction (UAE) of phenolic compounds from olive cake.

PubMed

Mojerlou, Zohreh; Elhamirad, Amirhhossein

2018-03-01

The use of ultrasound in ultrasound-assisted extraction (UAE) is one of the main applications of this technology in food industry. This study aimed to optimize UAE conditions for olive cake extract (OCE) through response surface methodology (RSM). The optimal UAE conditions were obtained with extraction temperature of 56 °C, extraction time of 3 min, duty cycle of 0.6 s, and solid to solvent ratio of 3.6%. At the optimum conditions, the total phenolic compounds (TPC) content and antioxidant activity (AA) were measured 4.04 mg/g and 68.9%, respectively. The linear term of temperature had the most effect on TPC content and AA of OCE prepared by UAE. Protocatechuic acid and cinnamic acid were characterized as the highest (19.5%) and lowest (1.6%) phenolic compound measured in OCE extracted by UAE. This research revealed that UAE is an effective method to extract phenolic compounds from olive cake. RSM successfully optimized UAE conditions for OCE.

Kinetic and Isotherm Modelling of the Adsorption of
Phenolic Compounds from Olive Mill Wastewater onto Activated Carbon

PubMed Central

Casazza, Alessandro A.; Perego, Patrizia

2015-01-01

Summary The adsorption of phenolic compounds from olive oil wastewater by commercial activated carbon was studied as a function of adsorbent quantity and temperature. The sorption kinetics and the equilibrium isotherms were evaluated. Under optimum conditions (8 g of activated carbon per 100 mL), the maximum sorption capacity of activated carbon expressed as mg of caffeic acid equivalent per g of activated carbon was 35.8 at 10 °C, 35.4 at 25 °C and 36.1 at 40 °C. The pseudo-second-order model was considered as the most suitable for kinetic results, and Langmuir isotherm was chosen to better describe the sorption system. The results confirmed the efficiency of activated carbon to remove almost all phenolic compound fractions from olive mill effluent. The preliminary results obtained will be used in future studies. The carbohydrate fraction of this upgraded residue could be employed to produce bioethanol, and adsorbed phenolic compounds can be recovered and used in different industries. PMID:27904350

Decoction, infusion and hydroalcoholic extract of Origanum vulgare L.: different performances regarding bioactivity and phenolic compounds.

PubMed

Martins, Natália; Barros, Lillian; Santos-Buelga, Celestino; Henriques, Mariana; Silva, Sónia; Ferreira, Isabel C F R

2014-09-01

Bioactivity of oregano methanolic extracts and essential oils is well known. Nonetheless, reports using aqueous extracts are scarce, mainly decoction or infusion preparations used for therapeutic applications. Herein, the antioxidant and antibacterial activities, and phenolic compounds of the infusion, decoction and hydroalcoholic extract of oregano were evaluated and compared. The antioxidant activity is related with phenolic compounds, mostly flavonoids, since decoction presented the highest concentration of flavonoids and total phenolic compounds, followed by infusion and hydroalcoholic extract. The samples were effective against gram-negative and gram-positive bacteria. It is important to address that the hydroalcoholic extract showed the highest efficacy against Escherichia coli. This study demonstrates that the decoction could be used for antioxidant purposes, while the hydroalcoholic extract could be incorporated in formulations for antimicrobial features. Moreover, the use of infusion/decoction can avoid the toxic effects showed by oregano essential oil, widely reported for its antioxidant and antimicrobial properties. Copyright © 2014 Elsevier Ltd. All rights reserved.

Sugar cane stillage: a potential source of natural antioxidants.

PubMed

Caderby, Emma; Baumberger, Stéphanie; Hoareau, William; Fargues, Claire; Decloux, Martine; Maillard, Marie-Noëlle

2013-11-27

Biorefinery of sugar cane is the first economic activity of Reunion Island. Some sugar cane manufactured products (juice, syrup, molasses) have antioxidant activities and are sources of both phenolic compounds and Maillard Reaction Products (MRP). The study aimed to highlight the global antioxidant activity of sugar cane stillage and understand its identity. Chromatographic fractionation on Sephadex LH-20 resin allowed the recovery of a MRP-rich fraction, responsible for 58 to 66% of the global antioxidant activity according to the nature of the sugar cane stillage (DPPH test), and a phenolic compounds-rich fraction for 37 to 59% of the activity. A good correlation was recorded between the antioxidant activity of the sugar cane stillage and its content in total reducing compounds amount (Folin-Ciocalteu assay), among them 2.8 to 3.9 g/L of phenolic compounds (in 5-caffeoylquinic acid equivalent). Preliminary experiments by HPLC-DAD-MS allowed to identify several free phenolic acids and gave clues to identify esters of quinic acids.

Polyvinylpolypyrrolidone reduces cross-reactions between antibodies and phenolic compounds in an enzyme-linked immunosorbent assay for the detection of ochratoxin A.

PubMed

Robinson, Andrew L; Lee, Hyun Jung; Ryu, Dojin

2017-01-01

Ochratoxin A (OTA) is a fungal metabolite and putative carcinogen which can contaminate a variety of foods such as cereals, wine, and nuts. Commercial ELISA kits are known to give false-positive results for OTA concentrations when phenolic compounds are present. Pistachios represent a food matrix rich in phenolic compounds potentially contaminated with OTA, and were used to model OTA cross-reactivity. Polyvinylpolypyrrolidone (PVPP) was incorporated during extraction of OTA using a commercial ELISA protocol. HPLC methods were used to confirm that PVPP does not interact with OTA and levels of gallic acid and catechin remaining in pistachio extracts decreased with increasing PVPP application. Cross-reactivity of extracts also decreased with increasing PVPP application, and color loss was used as an indicator of anthocyanin removal. Incorporating PVPP into ELISA protocols allows for the continued use of rapid immunological methods in food matrices containing phenolic compounds. Copyright © 2016 Elsevier Ltd. All rights reserved.

Polyphenols in strawberry (Fragaria × ananassa) leaves induced by plant activators.

PubMed

Kårlund, Anna; Salminen, Juha-Pekka; Koskinen, Piia; Ahern, Jeffrey R; Karonen, Maarit; Tiilikkala, Kari; Karjalainen, Reijo O

2014-05-21

Strawberry leaves contain high amounts of diverse phenolic compounds potentially possessing defensive activities against microbial pathogens and beneficial properties for human health. In this work, young strawberry plants were treated with two plant activators, S-methylbenzo-1,2,3-thaidiazole-7-carbothiate (BTH) and birch wood distillate. Phenolic compounds from activator-treated and control leaves were subjected to quantitative analyses by HPLC-DAD, HPLC-ESI-MS, and microQTOF ESI-MS. Thirty-two different phenolic compounds were detected and characterized, and 21 different ellagitannins constituted the largest group of compounds in the strawberry leaves (37.88-45.82 mg/g dry weight, 47.0-54.3% of total phenolics). Treatment with BTH resulted in higher levels of individual ellagitannins, whereas treatment with birch wood distillate strongly increased the levels of chlorogenic acid in strawberry leaves compared with the control. The results suggest that different plant activators may be useful tools for the activation of different branches in the phenylpropanoid biosynthesis in strawberry.

[The content of phenolic compounds and antioxidant activity ready to eat desserts for infants].

PubMed

Filipiak-Florkiewicz, Agnieszka; Dereń, Katarzyna

2011-01-01

The aim of this study was to determine the content of phenolic compounds and antioxidant activity in ready-to-eat desserts for babies. The experimental material consisted of six kinds of fruit desserts taken from the market in 2008, in which the content of dry matter phenolic compounds and antioxidant activity levels on the basis of free radical quenching ability ABTS were determined. The largest share of dry matter was found in apricot mousse with apples and bananas (16.9%). The largest amounts of phenolic compounds were found in the cream with apple and wild rose (186.3 mg/100 g) and apple with forest fruits (170.7 mg/100 g). The highest antioxidant activity among the desserts was determined in cream with apple and wild rose (14.2 micromol Trolox/g) and apple mousse with peaches (12.8 micromol Trolox/g). The antioxidant capacity of the remaining examined purée was slightly lower and ranged from 11.4-11.7 micromol Trolox/g.

Development of electrospun nanofibers containing chitosan/PEO blend and phenolic compounds with antibacterial activity.

PubMed

Kuntzler, Suelen Goettems; Costa, Jorge Alberto Vieira; Morais, Michele Greque de

2018-05-31

Electrospun nanofibers can be formed with chitosan as the polymers found in biological sources have antibacterial ability. The objective of this work was to evaluate whether chitosan/polyethylene oxide (PEO) blend nanofibers containing microalgal phenolic compounds exhibit antibacterial activity. Nanofibers produced with a 3% chitosan/2% PEO blend containing 1% phenolic compounds had an average diameter of 214 ± 37 nm, which resulted in a high temperature of maximum degradation, an important parameter for food packaging. The potential antibacterial activity of this nanofibers was confirmed by their inhibition of Staphylococcus aureus ATCC 25923 (6.4 ± 1.1 mm) and Escherichia coli ATCC 25972 (5.5 ± 0.4 mm). The polymeric nanofibers produced from chitosan and containing phenolic compounds have properties that therefore allow their application as active packaging. In addition, chitosan is an excellent polymer for packaging as it presents biodegradability, biocompatibility and, non-toxicity. Copyright © 2018. Published by Elsevier B.V.

Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII).

PubMed

Scozzafava, Andrea; Passaponti, Maurizio; Supuran, Claudiu T; Gülçin, İlhami

2015-01-01

Carbonic anhydrases (CAs) are widespread metalloenzymes in higher vertebrates including humans. A series of phenolic compounds, including guaiacol, 4-methylguaiacol, 4-propylguaiacol, eugenol, isoeugenol, vanillin, syringaldehyde, catechol, 3-methyl catechol, 4-methyl catechol and 3-methoxy catechol were investigated for their inhibition of all the catalytically active mammalian isozymes of the Zn(2+)-containing CA (EC 4.2.1.1). All the phenolic compounds effectively inhibited human carbonic anhydrase isoenzymes (hCA I, II, IX and XII), with Kis in the range of 2.20-515.98 μM. The various isozymes showed diverse inhibition profiles. Among the tested phenolic derivatives, compounds 4-methyl catechol and 3-methoxy catechol showed potent activity as inhibitors of the tumour-associated transmembrane isoforms (hCA IX and XII) in the submicromolar range, with high selectivity. The results obtained from this research may lead to the design of more effective carbonic anhydrase isoenzyme inhibitors (CAIs) based on such phenolic compound scaffolds.

Catalytic ozonation of aqueous phenol over metal-loaded HZSM-5.

PubMed

Amin, Nor Aishah Saidina; Akhtar, Javaid; Rai, H K

2011-01-01

The performances of HZSM-5 and transition metal-loaded HZSM-5 (Mn, Cu, Fe, Ti) catalysts during catalytic ozonation of phenol have been investigated. It was observed the performance order for removal of phenol and COD was Mn/HZSM-5 > Fe/HZSM-5 > Cu/HZSM-5 > Ti/HZSM-5 > HZSM-5. The presence of metals on HZSM-5 enhanced the phenol removal capability of HZSM-5. Mn loading on HZSM-5 was optimized due to its high phenol removal capability amongst metal-loaded HZSM-5 catalysts. Experimental results suggested that low amount of Mn loading on HZSM-5 was sufficient for HZSM-5 to act as catalyst and adsorbent. A maximum of 95.8 wt% phenols and 70.2 wt% COD were removed over 2 wt% Mn/HZSM-5 in 120 min. It was supposed that transition metals mainly acted as ozone decomposers due to their multiple oxidation states that enhanced the ozonation of phenol.

Fabrication of polyaniline-coated halloysite nanotubes by in situ chemical polymerization as a solid-phase microextraction coating for the analysis of volatile organic compounds in aqueous solutions.

PubMed

Abolghasemi, Mir Mahdi; Arsalani, Naser; Yousefi, Vahid; Arsalani, Mahmood; Piryaei, Marzieh

2016-03-01

We have synthesized an organic-inorganic polyaniline-halloysite nanotube composite by an in situ polymerization method. This nanocomposite is immobilized on a stainless-steel wire and can be used as a fiber coating for solid-phase microextraction. It was found that our new solid-phase microextraction fiber is an excellent adsorbent for the extraction of some volatile organic compounds in aqueous samples in combination with gas chromatography and mass spectrometry. The coating can be prepared easily, is mechanically stable, and exhibits relatively high thermal stability. It is capable of extracting phenolic compounds from water samples. Following thermal desorption, the phenols were quantified by gas chromatography with mass spectrometry. The effects of extraction temperature, extraction time, sample ionic strength, stirring rate, pH, desorption temperature and desorption time were studied. Under optimal conditions, the repeatability for one fiber (n = 5), expressed as the relative standard deviation, is between 6.2 and 9.1%. The detection limits range from 0.005 to 4 ng/mL. The method offers the advantage of being simple to use, with a shorter analysis time, lower cost of equipment and higher thermal stability of the fiber in comparison to conventional methods of analysis. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection.

PubMed

Kahoun, David; Rezková, Sona; Veskrnová, Katerina; Královský, Josef; Holcapek, Michal

2008-08-15

The objective of this study was the determination of 25 phenolic compounds in different mead samples (honeywines) using high performance liquid chromatography (HPLC) with coulometric-array detection and in case of hydroxymethylfurfural with UV detection. Our method was optimized in respect to both the separation selectivity of individual phenolic compounds and the maximum sensitivity with the electrochemical detection. The method development included the optimization of mobile phase composition, the pH value, conditions of the gradient elution and the flow rate using a window-diagram approach. The developed method was used for the determination of limits of detection and limits of quantitation for individual compounds. The linearity of calibration curves, accuracy and precision (intra- and inter-day) at three concentration levels (low, middle and high concentration range) were verified. Mead samples were diluted with the mobile phase at 1:1 to 1:50 ratio depending on the concentration and filtered through a PTFE filter without any other sample pre-treatment. Phenolic compounds concentration was determined in 50 real samples of meads and correlated with meads composition and hydroxymethylfurfural concentration. The most frequently occurred compounds were protocatechuic acid and vanillic acid (both of them were present in 98% samples), the least occurred compounds were (+)-catechin (10% samples) and sinapic acid (12% samples). Vanillin and ethylvanillin, which are used as artificial additives for the taste improvement, were found in 60% and 42% samples, respectively. Hydroxymethylfurfural concentration, as an indicator of honey quality, was in the range from 2.47 to 158 mg/L. Our method is applicable for the determination of 25 phenolic compounds in mead, honey and related natural samples.

Characterisation of phenolic compounds by HPLC-TOF/IT/MS in buds and open flowers of 'Chemlali' olive cultivar.

PubMed

Taamalli, Amani; Abaza, Leila; Arráez Román, David; Segura Carretero, Antonio; Fernández Gutiérrez, Alberto; Zarrouk, Mokhtar; Nabil, Ben Youssef

2013-01-01

Plant phenolics are secondary metabolites that constitute one of the most widely occurring groups of phytochemicals that play several important functions in plants. In olive (Olea europaea L), there is not enough information about the occurrence of these compounds in buds and flowers. To conduct a comprehensive characterisation of buds and open flowers from the olive cultivar 'Chemlali'. The polar fraction of buds and open flowers was extracted using solid-liquid extraction with hydro-alcoholic solvent. Then extracts were analysed using high performance liquid chromatography (HPLC) coupled to electrospray ionisation time-of-flight mass spectrometry (ESI/TOF/MS) and electrospray ionisation ion-trap tandem mass spectrometry (ESI/IT/MS²) operating in negative ion mode. Phenolic compounds from different classes including secoiridoids, flavonoids, simple phenols, cinnamic acid derivatives and lignans were tentatively identified in both extracts. Qualitatively, no significant difference was observed between flower buds and open flowers extracts. However, quantitatively the secoiridoids presented higher percentage of total phenols in open flowers (41.7%) than in flower buds (30.5%) in contrast to flavonoids, which decreased slightly from 38.1 to 26.7%. Cinnamic acid derivatives and simple phenols did not show any change. Lignans presented the lowest percentage in both extracts with an increase during the development of the flower bud to open flower. The HPLC-TOF/IT/MS allowed the characterisation, for the first time, of the phenolic profile of extracts of 'Chemlali' olive buds and open flowers, proving to be a very useful technique for the characterisation and structure elucidation of phenolic compounds. Copyright © 2013 John Wiley & Sons, Ltd.

Effect of olive cultivar on bioaccessibility and antioxidant activity of phenolic fraction of virgin olive oil.

PubMed

Quintero-Flórez, Angélica; Pereira-Caro, Gema; Sánchez-Quezada, Cristina; Moreno-Rojas, José Manuel; Gaforio, José J; Jimenez, Antonio; Beltrán, Gabriel

2017-06-05

This study aims to characterize the phenolic profile and antioxidant capacity of seven monovarietal virgin olive oils (VOOs) and evaluate their in vitro gastrointestinal stability. 'Picual', 'Blanqueta', 'Sevillana', 'Habichuelero', and 'Chetoui' olive cultivars were selected for VOO extraction. The oils were subjected to in vitro digestion. The recovery index (RI) of phenolic compounds after each digestion step and the bioaccessibility index (BI) were evaluated. In addition, the antioxidant activity of the bioaccessible fraction (BF) of VOOs was determined by DPPH, ABTS, and ORAC assays, as well as by studying the intracellular reactive oxygen species in Caco-2 cells. Differences were found in the composition of phenolic compounds in VOOs depending on cultivars. During the digestive process, important losses of phenolic compounds were observed between the buccal and duodenal steps, unlike HTy and Ty, which presented increased recovery due to the hydrolysis of secoiridoid derivatives. Differences in the bioaccessibility of phenolic compounds were found between varieties of VOOs. 'Sevillana' VOO had the highest total bioaccessibility (36%), followed by the 'Picual' (19%), 'Chetoui' (17%), 'Habichuelero' (10%), and 'Blanqueta' (8%) varieties. The BF of all the varieties of VOO showed similar radical ABTS scavenging capacity, 'Chetoui', and 'Blanqueta'-BF having the highest radical DPPH scavenging capacity, and 'Habichuelero' and 'Picual'-BF showing protective effects against the peroxyl radical measured by ORAC FL assay. All VOO-BFs presented decreases in ROS levels in Caco-2 cells. Our results suggest differences in the bioaccessibility of phenolics from diverse VOO varieties, which could lead to different biological properties. Therefore, this study represents a first step toward the development of novel dietary strategies focusing on the phenolic supplementation of different VOOs to preserve human health.

Interactive effects of aluminum and cadmium on phenolic compounds, antioxidant enzyme activity and oxidative stress in blueberry (Vaccinium corymbosum L.) plantlets cultivated in vitro.

PubMed

Manquián-Cerda, K; Cruces, E; Escudey, M; Zúñiga, G; Calderón, R

2018-04-15

To evaluate the potential role of phenolic compounds in Al and Cd stress tolerance mechanisms, Vaccinium corymbosum cv. Legacy plantlets were exposed to different metal concentrations. The present study used an in vitro plant model to test the effects of the following treatments: 100μM Al; 100μMAl + 50μMCd; and 100μMAl + 100μMCd during periods of 7, 14, 21 and 30 days. The oxidative damage was determined by the accumulation of malondialdehyde (MDA) and hydrogen peroxide (H 2 O 2 ). The antioxidant activity values were determined using 1,1-diphenyl-2-picrylhydrazine (DPPH) and the ferric reducing antioxidant power test (FRAP). Additionally, the phenolic compound concentrations were determined using HPLC-DAD. The exposure to Al and Cd increased the MDA and H 2 O 2 contents differentially, while the antioxidant capacity values showed differences between DPPH and FRAP with the largest changes in FRAP relative to Cd. SOD had the highest activity in the first 7 days, leading to a significant increase in phenolic compounds observed after 14 days, and chlorogenic acid was the major compound identified. Our results revealed that phenolic compounds seem to play an important role in the response to ROS. Therefore, the mechanisms of tolerance to Al and Cd in V. corymbosum will be determined by the type of metal and time of exposure. Copyright © 2017 Elsevier Inc. All rights reserved.

Characterisation of antioxidant compounds in sweet bell pepper (Capsicum annuum L.) under organic and conventional growing systems.

PubMed

Hallmann, Ewelina; Rembiałkowska, Ewa

2012-09-01

Sweet red bell pepper is one of the best sources of ascorbic acid and carotenoids as well as phenolic compounds important in the human diet. There have been some studies showing a higher level of bioactive compounds in organic bell pepper fruits compared with conventional fruits, but not all studies have been consistent in this respect. The levels of carotenoids and phenolics are very variable and may be affected by ripeness, genotype and cultivation. The results obtained in this study showed that an organic growing system affected the level of bioactive compounds (carotenoids and polyphenols) in sweet bell pepper fruits cultivated in Poland. Organic bell pepper fruits contained significantly more dry matter, vitamin C, total carotenoids, β-carotene, α-carotene, cis-β-carotene, total phenolic acids (as well as individual gallic and chlorogenic acids) and flavonoids (quercetin D-glucoside, quercetin and kaempferol) compared with conventional fruits. The bell pepper variety also affected the level of antioxidant compounds in fruits. Organic growing increased the level of antioxidant compounds such as carotenoids, phenolic compounds and vitamin C in sweet bell pepper. The second significant factor affecting the antioxidant compound content of sweet bell pepper was variety. It would be necessary to continue this study as a long-term experiment in order to eliminate the influence of seasonality. Copyright © 2012 Society of Chemical Industry.

Humic-like Products Formation via the Reaction of Phenol with Nitrite in Ice Phase

NASA Astrophysics Data System (ADS)

Min, D. W.; Choi, W.

2017-12-01

Understanding the chemical nature of humic substances is very important but the origin of humic substances in nature is not well known. Therefore, elucidating the mechanisms leading to the generation of humic substances in nature is of great interests. It is believed that humic substances are produced from the transformation of natural organic matters, like lignin, by biological pathways. Recently, it has been reported that monomer molecules like quinones and sugars could be polymerized with amino compounds to form humic-like substances. This humification process is considered as a possible mechanism of humic substances production in the environment. In this work, we report the first observation on the formation of humic-like substances from the reaction between phenol and nitrite under a frozen state. In aqueous solution, nitrite slowly reacts with phenol, producing phenolic compounds like nitrophenol. Under frozen state, however, phenol reacted rapidly with nitrite and produced diverse organic compounds, like hydroquinone, dimerized phenolic substances, and much bigger molecules such as humic-like substances. The humic-like substances produced in ice are likely caused by the formation of phenolic radical and nitrosonium ion. This work may provide some insights into unknown pathways for the origin of humic substances especially in frozen environments.

A comparison of the phenolic profile and antioxidant activity of different Cichorium spinosum L. ecotypes.

PubMed

Petropoulos, Spyridon A; Fernandes, Ângela; Barros, Lillian; Ferreira, Isabel Cfr

2018-01-01

Wild greens are considered a rich source of phenolic compounds and antioxidants and an essential part of the so-called Mediterranean diet. In the present study, Cichorium spinosum L. ecotypes, cultivated or collected in situ from wild plants from the eastern Mediterranean, were evaluated regarding their phenolic composition and antioxidant activity. Significant differences were observed among the various studied ecotypes regarding their phenolic compound content and profile, especially between wild and cultivated ecotypes, as well as the phenolic acid content between commercial products and cultivated plants. The antioxidant activity also varied among the various studied ecotypes and growing conditions, with commercial products having the highest antioxidant activity, whereas wild ecotypes showed lower antioxidant activity. Cichorium spinosum leaves are a rich source of chicoric and 5-O-caffeoylquinic acid, while significant differences in total phenolic acids, flavonoids and phenolic compound content and in antioxidant activity were observed among the studied ecotypes, as well as between the tested growing conditions. According to the results of the present study, further valorization of C. spinosum species has great potential, since it could be used as a new alternative species in the food industry. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Growth and phenolic compounds of Lactuca sativa L. grown in a closed-type plant production system with UV-A, -B, or -C lamp.

PubMed

Lee, Min-Jeong; Son, Jung Eek; Oh, Myung-Min

2014-01-30

The production of high-quality crops based on phytochemicals is a strategy for accelerating the practical use of plant factories. Previous studies have demonstrated that ultraviolet (UV) light is effective in improving phytochemical production. This study aimed to determine the effect of various UV wavelengths on growth and phenolic compound accumulation in lettuce (Lactuca sativa L.) grown in a closed-type plant production system. Seven days, 1 day and 0.25 day were determined as the upper limit of the irradiation periods for UV-A, -B, and -C, respectively, in the lettuce based on physiological disorders and the fluorescence parameter F(v)/F(m). Continuous UV-A treatment significantly induced the accumulation of phenolic compounds and antioxidants until 4 days of treatment without growth inhibition, consistent with an increase in phenylalanine ammonia lyase (PAL) gene expression and PAL activity. Repeated or gradual UV-B exposure yielded approximately 1.4-3.6 times more total phenolics and antioxidants, respectively, than the controls did 2 days after the treatments, although both treatments inhibited lettuce growth. Repeated UV-C exposure increased phenolics but severely inhibited the growth of lettuce plants. Our data suggest that UV irradiation can improve the accumulation of phenolic compounds with antioxidant properties in lettuce cultivated in plant factories. © 2013 Society of Chemical Industry.

Use of Polyphenolic Compounds in Dermatologic Oncology

PubMed Central

Costa, Adilson; Bonner, Michael Yi

2017-01-01

Polyphenols are a widely used class of compounds in dermatology. While phenol itself, the most basic member of the phenol family, is chemically synthesized, most polyphenolic compounds are found in plants and form part of their defense mechanism against decomposition. Polyphenolic compounds, which include phenolic acids, flavonoids, stilbenes, and lignans, play an integral role in preventing the attack on plants by bacteria and fungi, as well as serving as cross-links in plant polymers. There is also mounting evidence that polyphenolic compounds play an important role in human health as well. One of the most important benefits, which puts them in the spotlight of current studies, is their antitumor profile. Some of these polyphenolic compounds have already presented promising results in either in vitro or in vivo studies for non-melanoma skin cancer and melanoma. These compounds act on several biomolecular pathways including cell division cycle arrest, autophagy, and apoptosis. Indeed, such natural compounds may be of potential for both preventive and therapeutic fields of cancer. This review evaluates the existing scientific literature in order to provide support for new research opportunities using polyphenolic compounds in oncodermatology. PMID:27164914

Recovery and concentration of antioxidants from winery wastes.

PubMed

Soto, María Luisa; Conde, Enma; González-López, Noelia; Conde, María Jesús; Moure, Andrés; Sineiro, Jorge; Falqué, Elena; Domínguez, Herminia; Núñez, María José; Parajó, Juan Carlos

2012-03-09

Grape and wine byproducts have been extensively studied for the recovery of phenolic compounds with antioxidant activity and a variety of biological actions. The selective recovery and concentration of the phenolic compounds from the liquid phase separated from further diluted winery wastes has been proposed. Adsorption onto non ionic polymeric resins and further desorption with ethanolic solutions was studied. Several commercial food grade resins were screened with the aim of selecting the most suited for the practical recovery of phenolic compounds with radical scavenging activity. Under the optimized desorption conditions (using Sepabeads SP207 or Diaion HP20 as adsorbents and eluting with 96% ethanol at 50 °C) a powdered yellow-light brown product with 50% phenolic content, expressed as gallic acid equivalents, was obtained. The radical scavenging capacity of one gram of product was equivalent to 2-3 g of Trolox.

Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.

PubMed Central

Miller, D; Wheals, B B; Beresford, N; Sumpter, J P

2001-01-01

We used a recombinant yeast estrogen assay to assess the activity of 73 phenolic additives that are used as sunscreens, preservatives, disinfectants, antioxidants, flavorings, or for perfumery. Thirty-two of these compounds displayed activity: 22 with potencies relative to 17beta-estradiol, ranging from 1/3,000 to < 1/3,000,000, and 10 compounds with an impaired response that could not be directly compared with 17beta-estradiol. Forty-one compounds were inactive. The major criteria for activity appear to be the presence of an unhindered phenolic OH group in a para position and a molecular weight of 140-250 Da. PMID:11266322

Berry Phenolic Antioxidants – Implications for Human Health?

PubMed Central

Olas, Beata

2018-01-01

Antioxidants present in the diet may have a significant effect on the prophylaxis and progression of various diseases associated with oxidative stress. Berries contain a range of chemical compounds with antioxidant properties, including phenolic compounds. The aim of this review article is to provide an overview of the current knowledge of such phenolic antioxidants, and to discuss whether these compounds may always be natural gifts for human health, based on both in vitro and in vivo studies. It describes the antioxidant properties of fresh berries (including aronia berries, grapes, blueberries, sea buckthorn berries, strawberries and other berries) and their various products, especially juices and wines. Some papers report that these phenolic compounds may sometimes behave like prooxidants, and sometimes demonstrate both antioxidant and prooxidant activity, while others note they do not behave the same way in vitro and in vivo. However, no unwanted or toxic effects (i.e., chemical, hematological or urinary effect) have been associated with the consumption of berries or berry juices or other extracts, especially aronia berries and aronia products in vivo, and in vitro, which may suggest that the phenolic antioxidants found in berries are natural gifts for human health. However, the phenolic compound content of berries and berry products is not always well described, and further studies are required to determine the therapeutic doses of different berry products for use in future clinical studies. Moreover, further experiments are needed to understand the beneficial effects reported so far from the mechanistic point of view. Therefore, greater attention should be paid to the development of well-controlled and high-quality clinical studies in this area. PMID:29662448

Phenolic profiles and their contribution to the antioxidant activity of selected chickpea genotypes from Mexico and ICRISAT collections.

PubMed

Quintero-Soto, Maria F; Saracho-Peña, Ana G; Chavez-Ontiveros, Jeanett; Garzon-Tiznado, Jose A; Pineda-Hidalgo, Karen V; Delgado-Vargas, Francisco; Lopez-Valenzuela, Jose A

2018-06-01

Chickpea (Cicer arietinum L.) genotypes, nine kabuli from Mexico and 9 desi from other countries, were investigated for their phenolic profiles and antioxidant activity (AA). Phenolics in methanol extracts (ME) were analyzed by ultra-performance liquid chromatography coupled to diode array detection and mass spectrometry (UPLC-DAD-MS), whereas the AA was measured as Trolox equivalents (TE) by ABTS, DPPH and FRAP methods. Twenty phenolic compounds were identified in the ME and their levels showed a great variability among the chickpea genotypes. Phenolic acids and flavonoids were the most abundant compounds in kabuli and desi genotypes, respectively. The AA values (μmol TE/ 100 g dw) by ABTS (278-2417), DPPH (52-1650), and FRAP (41-1181) were mainly associated with the content of sinapic acid hexoside, gallic acid, myricetin, quercetin, catechin, and isorhamnetin, suggesting they are the main compounds responsible for the AA. The sum of the AA obtained for standards of these compounds evaluated at the concentration found in the extracts accounted for 34.3, 69.8, and 47.0% of the AA in the extract by ABTS, DPPH, and FRAP, respectively. In the AA by DPPH, most of the mixtures of these compounds resulted in synergistic interactions. Three desi genotypes with black seeds (ICC 4418, ICC 6306, and ICC 3761) showed the highest AA and flavonoids content, whereas the most promising kabuli genotypes were Surutato 77, Bco. Sin. 92, and Blanoro that showed the highest values of phenolic acids. These genotypes represent good sources of antioxidants for the improvement of nutraceutical properties in chickpea.

Ferulic acid enhances IgE binding to peanut allergens in western blots.

USDA-ARS?s Scientific Manuscript database

Phenolic compounds at high concentrations are known to form insoluble complexes with proteins. We hypothesized that this complex formation could interfere with Western blot and ELISA assays for peanut allergens. To verify this, three simple phenolic compounds (ferulic, caffeic, and chlorogenic acids...

Analysis of phenolic compounds from corn, oat, and wheat bran extracts by LC-MS-PDA

USDA-ARS?s Scientific Manuscript database

Phenolic compounds are among the most common secondary metabolites produced by plants and can exhibit a range of bioactive properties including antimicrobial, antioxidant, and antihypertensive. These natural products have applications in nutraceutical, pharmaceutical and functional food or animal fe...

Anthocyanins and antioxidant activity in coloured waxy corn at different maturation stages

USDA-ARS?s Scientific Manuscript database

Concentrations of anthocyanins, phenolic compounds and antioxidant activities in kernels of 20 genotypes of waxy corn were investigated at two maturation stages, namely milky and mature. The levels of anthocyanins increased throughout the development of each genotype of corn, while phenolic compound...

RADIATION DOSIMETER

DOEpatents

Balkwell, W.R. Jr.; Adams, G.D. Jr.

1960-05-10

An improvement was made in the determination of amounts of ionizing radiation, particularly low-energy beta particles of less than 1000 rad total dose by means of fluid-phase dosimeter employing a stabilized-- sensitized ferrous-ferric colorimetric system in a sulphuric acid medium. The improvement in the dosimeter consists of adding to the ferrous-ferric system in concentrations of 10/sub -2/ to 10/sup -4/M an organic compound having one or more carboxylic or equivalent groups, such compounds being capable of chelating or complexing the iron ions in the solution. Suitable sensitizing and stabilizing agents are benzoic, phthalic, salicylic, malonic, lactic, maleic, oxalic, citric, succinic, phenolic tartaric, acetic, and adipic acid, as well as other compounds which are added to the solution alone or in certain combinations. As in conventional fluid-phase dosimeters, the absorbed dosage is correlated with a corresponding change in optical density at particular wavelengths of the solution.

Antioxidant capacity, polyphenolic content and tandem HPLC-DAD-ESI/MS profiling of phenolic compounds from the South American berries Luma apiculata and L. chequén.

PubMed

Simirgiotis, Mario J; Bórquez, Jorge; Schmeda-Hirschmann, Guillermo

2013-08-15

Native Myrtaceae fruits were gathered by South American Amerindians as a food source. At present, there is still some regional consume of the small berries from trees belonging to genus Luma that occurs in southern Chile and Argentina. The aerial parts and berries from Luma apiculata and Luma chequen were investigated for phenolic constituents and antioxidant capacity. A high performance electrospray ionisation mass spectrometry method was developed for the rapid identification of phenolics in polar extracts from both species. Thirty-one phenolic compounds were detected and 27 were identified or tentatively characterised based on photodiode array UV-vis spectra (DAD), ESI-MS-MS spectrometric data and spiking experiments with authentic standards. Twelve phenolic compounds were detected in L. apiculata fruits and 12 in the aerial parts while L. chequen yielded 10 compounds in fruits and 16 in aerial parts, respectively. From the compounds occurring in both Luma species, seven were identified as tannins or their monomers, 15 were flavonol derivatives and five were anthocyanins. The whole berry and aerial parts extracts presented high antioxidant capacity in the DPPH assay (IC50 of 10.41±0.02 and 2.44±0.03 μg/mL for L. apiculata, 12.89±0.05 and 3.22±0.05 for L. chequen, respectively), which can be related to the diverse range of phenolics detected. The antioxidant capacity together with the high polyphenolic contents and compounds identified can support at least in part, their use as botanical drugs. From the compounds identified in both species, 3-O-(6″-O-galloyl)-hexose derivatives of myricetin, quercetin, laricitrin and isorhamnetin are reported for the first time for the genus Luma. Copyright © 2013 Elsevier Ltd. All rights reserved.

Isolation and identification of some unknown substances in disposable nitrile-butadiene rubber gloves used for food handling.

PubMed

Mutsuga, M; Wakui, C; Kawamura, Y; Maitani, T

2002-11-01

In Japan, disposable gloves made from nitrile-butadiene rubber (NBR) are frequently used in contact with foods. In a previous paper, we investigated substances migrating from various gloves made of polyvinyl chloride, polyethylene, natural rubber and NBR. Zinc di-n-butyldithiocarbamate (ZDBC), diethyldithiocarbamate (ZDEC) used as vulcanization accelerators, di(2-ethylhexyl)phthalate (DEHP) used as a plasticizer and many unknown compounds that migrated from NBR gloves into n-heptane were detected by GC/MS. In this paper, six unknown compounds were obtained from one kind of NBR glove by n-hexane extraction and each was isolated by silica gel chromatography. From the results of NMR and mass spectral analysis of the six unknown compounds, their structures are proposed as 1,4-dione-2,5-bis(1,1-dimethylpropyl)cyclohexadiene (1), 2-(1,1-dimethylethyl)-4-(1,1,3,3-tetra methylbutyl)phenol (2), 2,6-bis(1,1-dimethylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol (3), 2,4-bis(1,1,3,3-tetramethylbutyl)phenol (4), 2-(1,1-dimethylethyl)4,6-bis(1,1,3,3-tetramethylbutyl)phenol (5) and 2,4,6-tris(1,1,3,3-tetramethylbutyl)phenol (6). Compound 1 was observed in five of the seven kinds of NBR gloves, and compounds 2-4 and 6, which are not listed in Chemical Abstract (CA), were present in four kinds of gloves.

Phenolic Compounds and Antioxidant Activity of Different Organs of Potentilla fruticosa L. from Two Main Production Areas of China.

PubMed

Yu, Danmeng; Pu, Wenjun; Li, Dengwu; Wang, Dongmei; Liu, Qiaoxiao; Wang, Yongtao

2016-09-01

This report compared the phenolic compounds and antioxidant activity of the leaves, flowers, and stems of Potentilla fruticosa L. collected from two main production areas of P. R. China (Taibai Mountains and the Qinghai Huzhu Northern Mountains). The results indicated that there were significant differences in the phenol contents and antioxidant activities among the different organs and between the two productions. High-performance liquid-chromatography analysis indicated that hyperoside, (+)-catechin, ellagic acid, and rutin were the primary compounds in leaves and flowers; for stems, the content of six phenolic compounds, from two productions, were the lowest. The 1,1-diphenyl-2-picryl hydrazyl (DPPH), 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) di-ammonium salt (ABTS), ferric reducing power (FRAP), lipid peroxidation assays, and microbial test system (MTS) were used to evaluate the antioxidant activity. The results demonstrated that the leaves from two productions exhibited powerful antioxidant activity than other organs, which did not significantly differ from that of the positive control (rutin), followed by the flowers and stems. The correlation between the content of phytochemicals and the antioxidant activities of different organs showed that the total phenol, tannin, hyperoside, and (+)-catechin contents may influence the antioxidant activity, and these compounds can be used as markers for the quality control of P. fruticosa. © 2016 Wiley-VHCA AG, Zürich.

Hydrogen sulfide oxidation by a microbial consortium in a recirculation reactor system: sulfur formation under oxygen limitation and removal of phenols.

PubMed

Alcantara, Sergio; Velasco, Antonio; Muñoz, Ana; Cid, Juan; Revah, Sergio; Razo-Flores, Elías

2004-02-01

Wastewater from petroleum refining may contain a number of undesirable contaminants including sulfides, phenolic compounds, and ammonia. The concentrations of these compounds must be reduced to acceptable levels before discharge. Sulfur formation and the effect of selected phenolic compounds on the sulfide oxidation were studied in autotrophic aerobic cultures. A recirculation reactor system was implemented to improve the elemental sulfur recovery. The relation between oxygen and sulfide was determined calculating the O2/S2- loading rates (Q(O2)/Q(S)2- = Rmt), which adequately defined the operation conditions to control the sulfide oxidation. Sulfur-producing steady states were achieved at Rmt ranging from 0.5 to 1.5. The maximum sulfur formation occurred at Rmt of 0.5 where 85% of the total sulfur added to the reactor as sulfide was transformed to elemental sulfur and 90% of it was recovered from the bottom of the reactor. Sulfide was completely oxidized to sulfate (Rmt of 2) in a stirred tank reactor, even when a mixture of phenolic compounds was present in the medium. Microcosm experiments showed that carbon dioxide production increased in the presence of the phenols, suggesting that these compounds were oxidized and that they may have been used as carbon and energy source by heterotrophic microorganisms present in the consortium.

Phenolic compounds increase the transcription of mouse intestinal maltase-glucoamylase and sucrase-isomaltase.

PubMed

Simsek, Meric; Quezada-Calvillo, Roberto; Nichols, Buford L; Hamaker, Bruce R

2017-05-24

Diverse natural phenolic compounds show inhibition activity of intestinal α-glucosidases, which may constitute the molecular basis for their ability to control systemic glycemia. Additionally, phenolics can modify mRNA expression for proteins involved in nutritional, metabolic or immune processes. To explore the possibility that phenolics can regulate the mRNA expression, enzymatic activity, and protein synthesis/processing of intestinal Maltase-Glucoamylase (MGAM) and Sucrase-Isomaltase (SI), small intestinal explants from Balb/c mice were cultured for 24 h in the presence or absence of gallic acid, caffeic acid, and (+)-catechin at 0.1, 0.5, and 1 mM. We measured the levels of MGAM and SI mRNA expression by qRT-PCR, maltase and sucrase activities by a standard colorimetric method and the molecular size distribution of MGAM and SI proteins by western blotting. mRNA expression for MGAM was induced by the three phenolic compounds at 0.1 mM. mRNA expression for SI was induced by caffeic and gallic acids, but not by (+)-catechin. Caffeic acid was the most effective inducer of mRNA expression of these enzymes. Total maltase and sucrase activities were not affected by treatment with phenolics. The proportion of high molecular size forms of MGAM was significantly increased by two of the three phenolic compounds, but little effect was observed on SI proteins. Thus, changes in the protein synthesis/processing, affecting the proportions of the different molecular forms of MGAM, may account for the lack of correlation between mRNA expression and enzymatic activity.

Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

PubMed Central

Alov, Petko; Tsakovska, Ivanka; Pajeva, Ilza

2015-01-01

For more than half a century free radical-induced alterations at cellular and organ levels have been investigated as a probable underlying mechanism of a number of adverse health conditions. Consequently, significant research efforts have been spent for discovering more effective and potent antioxidants / free radical scavengers for treatment of these adverse conditions. Being by far the most used antioxidants among natural and synthetic compounds, mono- and polyphenols have been the focus of both experimental and computational research on mechanisms of free radical scavenging. Quantum chemical studies have provided a significant amount of data on mechanisms of reactions between phenolic compounds and free radicals outlining a number of properties with a key role for the radical scavenging activity and capacity of phenolics. The obtained quantum chemical parameters together with other molecular descriptors have been used in quantitative structure-activity relationship (QSAR) analyses for the design of new more effective phenolic antioxidants and for identification of the most useful natural antioxidant phenolics. This review aims at presenting the state of the art in quantum chemical and QSAR studies of phenolic antioxidants and at analysing the trends observed in the field in the last decade. PMID:25547098

Computational studies of free radical-scavenging properties of phenolic compounds.

PubMed

Alov, Petko; Tsakovska, Ivanka; Pajeva, Ilza

2015-01-01

For more than half a century free radical-induced alterations at cellular and organ levels have been investigated as a probable underlying mechanism of a number of adverse health conditions. Consequently, significant research efforts have been spent for discovering more effective and potent antioxidants / free radical scavengers for treatment of these adverse conditions. Being by far the most used antioxidants among natural and synthetic compounds, mono- and polyphenols have been the focus of both experimental and computational research on mechanisms of free radical scavenging. Quantum chemical studies have provided a significant amount of data on mechanisms of reactions between phenolic compounds and free radicals outlining a number of properties with a key role for the radical scavenging activity and capacity of phenolics. The obtained quantum chemical parameters together with other molecular descriptors have been used in quantitative structure-activity relationship (QSAR) analyses for the design of new more effective phenolic antioxidants and for identification of the most useful natural antioxidant phenolics. This review aims at presenting the state of the art in quantum chemical and QSAR studies of phenolic antioxidants and at analysing the trends observed in the field in the last decade.

Phenolic Compounds Present Schinus terebinthifolius Raddi Influence the Lowering of Blood Pressure in Rats.

PubMed

de Lima Glória, Lorena; Barreto de Souza Arantes, Mariana; Menezes de Faria Pereira, Silvia; de Souza Vieira, Guilherme; Xavier Martins, Camilla; Ribeiro de Carvalho Junior, Almir; Antunes, Fernanda; Braz-Filho, Raimundo; José Curcino Vieira, Ivo; Leandro da Cruz, Larissa; Siqueira de Almeida Chaves, Douglas; de Paiva Freitas, Silvério; Barros de Oliveira, Daniela

2017-10-23

This study identified two phenolic compounds in Schinus terebinthifolius Raddi fruits: naringenin (first report in this species) and gallic acid. Their structures were elucidated by nuclear magnetic resonance (NMR) data (¹H-, 13 C-NMR) and a high-performance liquid chromatography (HPLC) technique. A high content of phenolics (659.21 mg of gallic acid equivalents/g of sample-Folin-Ciocalteau method) and total flavonoids (140.69 mg of rutin equivalents/g of sample-aluminum chloride method) were quantified in S. terebinthifolius , as well as high antioxidant activity (77.47%-2,2-diphenyl-1-picrylhydrazyl, DPPH method). The antihypertensive activity related to its phenolic content was investigated. After intravenous infusion in Wistar rats, these phenolics significantly reduced ( p < 0.05) the systolic, median, and diastolic arterial pressures of individuals. The rotarod test was performed to determine the mechanism of action of the sample vasorelaxant effect. It was found that its action exceeded that of the positive control used (diazepam). This confirmed the vasodilatory activity exerted by S. terebinthifolius fruits is related to the phenolic compounds present in the plant, which are potent antioxidants and inhibit oxidative stress, mainly in the central nervous system.

Phenols recovery after steam explosion of Olive Mill Solid Waste and its influence on a subsequent biomethanization process.

PubMed

Serrano, Antonio; Fermoso, Fernando G; Alonso-Fariñas, Bernabé; Rodríguez-Gutierrez, Guillermo; Fernandez-Bolaños, Juan; Borja, Rafael

2017-11-01

A promising source of high added value compounds is the Olive Mill Solid Waste (OMSW). The aim of this research was to evaluate the viability of a biorefinery approach to valorize OMSW through the combination of steam explosion, phenols extraction, and anaerobic digestion. Steam explosion treatment increased the total phenol content in the steam exploited OMSW, which was twice than that the total phenol content in raw OMSW, although some undesirable compounds were also formed. Phenol extraction allowed the recovery of 2098mg hydroxytyrosol per kg of OMSW. Anaerobic digestion allowed the partial stabilization of the different substrates, although it was not improved by the steam explosion treatment. The economic suitability of the proposed biorefinery approach is favorable up to a phenol extract price 90.7% lower than the referenced actual price of 520€/kg. Copyright © 2017 Elsevier Ltd. All rights reserved.

Free and Bound Phenolic Compound Content and Antioxidant Activity of Different Cultivated Blue Highland Barley Varieties from the Qinghai-Tibet Plateau.

PubMed

Yang, Xi-Juan; Dang, Bin; Fan, Ming-Tao

2018-04-11

In this study, the polyphenols composition and antioxidant properties of 12 blue highland barley varieties planted on the Qinghai-Tibet Plateau area were measured. The contents of the free, bound and total phenolic acids varied between 166.20-237.60, 170.10-240.75 and 336.29-453.94 mg of gallic acid equivalents per 100 g of dry weight (DW) blue highland barley grains, while the free and bound phenolic acids accounted for 50.09% and 49.91% of the total phenolic acids, respectively. The contents of the free, bound and total flavones varied among 20.61-25.59, 14.91-22.38 and 37.91-47.98 mg of catechin equivalents per 100 g of dry weight (DW) of blue highland barley grains, while the free and bound flavones accounted for 55.90% and 44.10% of the total flavones, respectively. The prominent phenolic compounds in the blue hulless barley grains were gallic acid, benzoic acid, syringic acid, 4-coumaric acid, naringenin, hesperidin, rutin, (+)-catechin and quercetin. Among these, protocatechuic acid, chlorogenic acid and (+)-catechin were the major phenolic compounds in the free phenolics extract. The most abundant bound phenolics were gallic acid, benzoic acid, syringic acid, 4-coumaric acid, benzoic acid, dimethoxybenzoic acid, naringenin, hesperidin, quercetin and rutin. The average contribution of the bound phenolic extract to the DPPH • free radical scavenging capacity was higher than 86%, that of free phenolic extract to the ABTS •+ free radical scavenging capacity was higher than 79%, and that of free phenolic (53%) to the FRAP antioxidant activity was equivalent to that of the bound phenol extract (47%). In addition, the planting environment exerts a very important influence on the polyphenol composition, content and antioxidant activity of blue highland barley. The correlation analysis showed that 2,4-hydroxybenzoic acid and protocatechuic acid were the main contributors to the DPPH • and ABTS •+ free radical scavenging capacity in the free phenolic extract, while chlorogenic acid, vanillic acid, ferulic acid and quercetin were the main contributors to the free radical scavenging capacity in the bound phenol extract. The study results show that the blue highland barley grains have rich phenolic compounds and high antioxidant activity, as well as significant varietal differences. The free and bound phenolic extracts in the blue hulless barley grains have an equivalent proportion in the total phenol, and co-exist in two forms. They can be used as a potential valuable source of natural antioxidants, and can aid in enhancing the development and daily consumption of foods relating to blue highland barley.

Profile and antioxidant activity of phenolic extracts from 10 crabapples (Malus wild species).

PubMed

Li, Nan; Shi, Junling; Wang, Kun

2014-01-22

Phenolic products are highly demanded by the food and cosmetics industries and consumers due to their high antioxidant activities. To evaluate the potential of crabapples (Malus wild species) in preparing phenolic extracts, fruits of 10 crabapples grown in China were separately extracted with 80% (v/v) ethanol and ethyl acetate and the phenolic profiles, polyphenol (PC) and flavonoid contents (FC), and antioxidant activities of the extracts were analyzed. Chlorogenic acid, (-)-epicatechin, rutin, hyperin, and phlorizin appeared as the major phenolic compounds in all phenolic extracts. Ethanol extracts had PC of 302.83-1265.94 mg GAE/100g and FC of 352.45-2351.74 mg RE/100g, being 4.17 and 4.49 times those obtained in ethyl acetate extracts and much higher than those previously reported in apples. Malus wild species appeared as rich sources of phenolic compounds with high antioxidant activity, especially when high chlorogenic acid and rutin contents are emphasized.

Home Cooking and Phenolics: Effect of Thermal Treatment and Addition of Extra Virgin Olive Oil on the Phenolic Profile of Tomato Sauces.

PubMed

Vallverdú-Queralt, Anna; Regueiro, Jorge; Rinaldi de Alvarenga, José Fernando; Torrado, Xavier; Lamuela-Raventos, Rosa M

2014-04-09

Tomato products are a key component of the Mediterranean diet, which is strongly related to a reduced risk of cardiovascular events. The effect of cooking time (15, 30, 45, and 60 min) and the addition of extra virgin olive oil (5 and 10%) on the phenolic content of tomato sauces was monitored using liquid chromatography coupled to tandem mass spectrometry. Concentration of phenolics in the tomato sauces decreased during the cooking process, with the exception of caffeic acid and tyrosol. The main degradation observed was the oxidation of quercetin, since the hydroxy-function at the C-ring of this flavonoid is not blocked by a sugar moiety, unlike rutin. Higher levels of virgin olive oil in tomato sauce seemed to enhance the extraction of phenolic compounds from the tomato, leading to higher phenolic contents in the sauces. Thus, the food matrix containing the phenolic compounds plays a crucial role in determining their accessibility.

Evaluation of antioxidant activity, total phenolics, total flavonoids and LC-MS/MS characterisation of phenolic constituents in Stachys lavandulifolia.

PubMed

Rahimi Khoigani, Soroush; Rajaei, Ahmad; Goli, Sayed Amir Hossein

2017-02-01

The aim of this study was to evaluate phenolics profile and antioxidant activity of Stachys lavandulifolia. Total phenolics (TP), total flavonoids (TF), DPPH• assay (IC50), ferric ion reducing antioxidant power (FRAP) and total antioxidant capacity (TAC) of the methanolic extract were measured. The content of TP, TF, IC50, FRAP and TAC, were obtained as 16.59 gallic acid equiv./g dry matter (DM), 4.48 mg quercetin equiv./g DM, 2.07 (μg/mL), 0.014 (absorbance/mg phenolic) and 14.61 (mg BHT equiv./g DM), respectively. The results showed that S. lavandulifolia, compared to other species of Stachys, had moderate TP content with desirable antioxidant activity. Subsequently, 59 various phenolic compounds were identified and confirmed in the methanolic extract of S. lavandulifolia using high mass accuracy by MS2 experiments. The compounds consisted of 6 hydroxybenzoic acids and hydroxybenzoic aldehydes, 9 hydroxycinnamic acids, 1 coumarin, 32 flavonoids, 3 lignans, 2 stilbenes, 3 tannins and 3 other phenolics.

Identification of Natural Antimicrobial Substances in Red Muscadine Juice against Enterobacter sakazakii

USDA-ARS?s Scientific Manuscript database

Red muscadine (Vitis rotundifolia Michx.) juices with natural organic, phenolic acids and polyphenol compounds were tested against Cronobacter sakazakii. The concentration of total phenolic compounds of commercial baby juices ranged from 176.7 to 347.7 mg/mL. Commercial baby juices showed poor antim...

Mechanism of dehydration of phenols on nobel metals using first-principles micokinetic modeling

USDA-ARS?s Scientific Manuscript database

Phenolic compounds constitute a sizable fraction of depolymerized biomass and are an ideal feedstock for the production of chemicals such as benzene and toluene. However, these compounds require catalytic upgrade via hydrodeoxygenation (HDO), a process whereby oxygen is removed as water by adding hy...

COLBALT-MEDIATED ACTIVATION OF PEROXYMONOSULFATE AND SULFATE RADICAL ATTACK ON PHENOLIC COMPOUNDS, IMPLICATIONS OF CHLORIDE IONS

EPA Science Inventory

This study reports on the sulfate radical pathway of room temperature degradation of two phenolic compounds in water. The radicals were produced by the cobalt-mediated decomposition of peroxymonosulfate (Oxone) in an aqueous homogeneous system. The major intermediates formed from...

Anthocyanin, phenolics and antioxidant activity changes in purple waxy corn as affected by traditional cooking

USDA-ARS?s Scientific Manuscript database

Antioxidant components, including anthocyanins and phenolic compounds, antioxidant activity, and their changes during traditional cooking of fresh purple waxy corn were investigated. As compared to the raw corn, thermal treatment caused significant (p < 0.05) decreases in each antioxidant compound a...

Phenolic compounds from Byrsonima crassifolia L. bark: phytochemical investigation and quantitative analysis by LC-ESI MS/MS.

PubMed

Maldini, Mariateresa; Montoro, Paola; Pizza, Cosimo

2011-08-25

Phytochemical investigation of the methanolic extract of Byrsonima crassifolia's bark led to the isolation of 8 known phenolic compounds 5-O-galloylquinic acid, 3-O-galloylquinic acid, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, (+)-epicatechin-3-gallate along with (+)-catechin and (+)-epicatechin. Due to their biological value, in the present study, a high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, working in multiple reaction monitoring (MRM) mode, has been developed to quantify these compounds. B. crassifolia bark resulted in a rich source of phenolic compounds and particularly of galloyl derivates. The proposed analytical method is promising to be applied to other galloyl derivatives to quantify these bioactive compounds in raw material and final products. Copyright © 2011 Elsevier B.V. All rights reserved.

Oxygen compounds in the Irati Shale oil

DOE Office of Scientific and Technical Information (OSTI.GOV)

Alfonso, J.C.; Schmal, M.; Cardoso, J.N.

1992-04-01

This paper reports the principal alkylphenols (4 wt %) and carboxylic acids (1.2 wt %) present in the Irati Shale oil S[tilde a]o Mateus do Sul, Paran acute (a) by means of a combination of gas chromatography-mass spectrometry (GC-MS) and retention time-data of standard compounds. it appears that the phenols are essentially monocyclic in nature with methyl groups as the main substituents. Carboxylic acids are principally linear and predominantly of the range C[sub 14]--C[sub 20]. After catalytic hydrotreatment (400 [degrees]C, 125 atm) high hydrodeoxygenation levels were obtained (87 wt %) for phenols and carboxylic acids, although the relative distribution ofmore » the various compounds was not significantly changed. Oxygen is present in the carbonaceous residue as several functionalities xanthenes, phenols, aryl ethers, carbonyl compounds, and furanic structures. The remaining acidic compounds may cause instability of the treated shale oil.« less

Bioactivity-guided isolation of anticancer agents from Bauhinia kockiana Korth.

PubMed

Chew, Yik Ling; Lim, Yau Yan; Stanslas, Johnson; Ee, Gwendoline Cheng Lian; Goh, Joo Kheng

2014-01-01

Flowers of Bauhinia kockiana were investigated for their anticancer properties. Gallic acid (1), and methyl gallate (2), were isolated via bioassay-directed isolation, and they exhibited anticancer properties towards several cancer cell lines, examined using MTT cell viability assay. Pyrogallol (3) was examined against the same cancer cell lines to deduce the bioactive functional group of the phenolic compounds. The results showed that the phenolic compounds could exhibit moderate to weak cytotoxicity towards certain cell lines (GI50 30 - 86 µM), but were inactive towards DU145 prostate cancer cell (GI50 > 100 µM). It was observed that pyrogallol moiety was one of the essential functional structures of the phenolic compounds in exhibiting anticancer activity. Also, the carboxyl group of compound 1 was also important in anticancer activity. Examination of the PC-3 cells treated with compound 1 using fluorescence microscopy showed that PC-3 cells were killed by apoptosis.

Organically grown tomato (Lycopersicon esculentum Mill.): bioactive compounds in the fruit and infection with Phytophthora infestans.

PubMed

Mohammed, Afrah E; Smit, Inga; Pawelzik, Elke; Keutgen, Anna J; Horneburg, Bernd

2012-05-01

Tomato fruits are characterized by a good nutritional profile, including different bioactive compounds such as carotenoids, phenolic compounds and ascorbic acid. The objective of this study was to analyze the content of bioactive compounds in the fruit and the infection by Phytophthora infestans of 28 tomato genotypes from organic outdoor production. The relationship between bioactive compounds in the fruit and infection with P. infestans was estimated. Field experiments were carried out in 2004 and 2005 at two locations in central Germany. Significant variation among genotypes, locations and years was observed for the content of lycopene, ascorbic acid, total phenolic compounds, antioxidant capacity and the infection level of P. infestans. Antioxidant capacity seemed to be influenced mainly by the phenolics and was highest in small fruits, which were less infected with P. infestans. The large genetic variation among tomato genotypes for the content of bioactive compounds in their fruit allows for selection gains. None of the investigated bioactive compounds can be recommended for the indirect selection for increased field resistance against P. infestans. Copyright © 2011 Society of Chemical Industry.

Phenolics and compartmentalization in the sapwood of broad-leaved trees

Treesearch

Kevin T. Smith

1997-01-01

Tree survival depends on the chemistry of phenolic compounds, a broad class of chemicals characterized by a hydroxylated benzene ring. In trees, phenolics occur frequently as polymers, acids, or glycosylated esters and perform diverse functions. For example, lignin, a phenylpropane heteropolymer, provides structural strength to wood. The induced production of phenols...

Pilot-scale resin adsorption as a means to recover and fractionate apple polyphenols.

PubMed

Kammerer, Dietmar R; Carle, Reinhold; Stanley, Roger A; Saleh, Zaid S

2010-06-09

The purification and fractionation of phenolic compounds from crude plant extracts using a food-grade acrylic adsorbent were studied at pilot-plant scale. A diluted apple juice concentrate served as a model phenolic solution for column adsorption and desorption trials. Phenolic concentrations were evaluated photometrically using the Folin-Ciocalteu assay and by HPLC-DAD. Recovery rates were significantly affected by increasing phenolic concentrations of the feed solutions applied to the column. In contrast, the flow rate during column loading hardly influenced adsorption efficiency, whereas the temperature and pH value were shown to be crucial parameters determining both total phenolic recovery rates and the adsorption behavior of individual polyphenols. As expected, the eluent composition had the greatest impact on the desorption characteristics of both total and individual phenolic compounds. HPLC analyses revealed significantly different elution profiles of individual polyphenols depending on lipophilicity. This technique allows fractionation of crude plant phenolic extracts, thus providing the opportunity to design the functional properties of the resulting phenolic fractions selectively, and the present study delivers valuable information with regard to the adjustment of individual process parameters.

Review of various treatment methods for the abatement of phenolic compounds from wastewater.

PubMed

Girish, C R; Murty, V Ramachandra

2012-04-01

Phenol and its derivatives are considered among the most hazardous organic pollutants from industrial wastewater and they are toxic even at low concentrations. Besides the existence of phenol in natural water source it can lead to the formation of other toxic substituted compounds. So this has led to growing concern on setting up of rigid limits on the acceptable level of phenol in the environment. The various methods for the treatment of phenol from wastewater streams are briefly reviewed. The various technologies like distillation, liquid-liquid extraction with different solvents, adsorption over activated carbons and polymeric and inorganic adsorbents, membrane pervaporation and membrane-solvent extraction, have been elucidated. The advantages and disadvantages of the various methods are illustrated and their performances are compared.

Effects of plant antimicrobial phenolic compounds on virulence of the genus Pectobacterium.

PubMed

Joshi, Janak Raj; Burdman, Saul; Lipsky, Alexander; Yedidia, Iris

2015-01-01

Pectobacterium spp. are among the most devastating necrotrophs, attacking more than 50% of angiosperm plant orders. Their virulence strategy is based mainly on the secretion of exoenzymes that degrade the cell walls of their hosts, providing nutrients to the bacteria, but conversely, exposing the bacteria to plant defense compounds. In the present study, we screened plant-derived antimicrobial compounds, mainly phenolic acids and polyphenols, for their ability to affect virulence determinants including motility, biofilm formation and extracellular enzyme activities of different Pectobacteria: Pectobacterium carotovorum, P. brasiliensis, P. atrosepticum and P. aroidearum. In addition, virulence assays were performed on three different plant hosts following exposure of the bacteria to selected phenolic compounds. These experiments showed that cinnamic, coumaric, syringic and salicylic acids and catechol can considerably reduce disease severity, ranging from 20 to 100%. The reduced disease severity was not only the result of reduced bacterial growth, but also of a direct effect of the compounds on important bacterial virulence determinants, including pectolytic and proteolytic exoenzyme activities, that were reduced by 50-100%. This is the first report revealing a direct effect of phenolic compounds on virulence factors in a wide range of Pectobacterium strains. Copyright © 2015 Institut Pasteur. Published by Elsevier Masson SAS. All rights reserved.

Quorum Quenching and Microbial Control through Phenolic Extract of Eugenia Uniflora Fruits.

PubMed

Rodrigues, Adeline Conceição; Zola, Flávia Guimarães; Ávila Oliveira, Brígida D'; Sacramento, Nayara Thais Barbosa; da Silva, Elis Regina; Bertoldi, Michele Corrêa; Taylor, Jason Guy; Pinto, Uelinton Manoel

2016-10-01

We describe the characterization of the centesimal composition, mineral and phenolic content of Eugenia uniflora fruit and the determination of the antioxidant, antimicrobial and quorum quenching activities of the pulp phenolic extract. Centesimal composition was determined according to standard methods; trace elements were measured by total reflection X-ray fluorescence spectroscopy. The phenolic compounds were extracted by solid-phase chromatography and quantified by spectrophotometry. Antioxidant activity was determined by using 3 different methods. Antimicrobial activity was evaluated against a panel of foodborne microorganisms and antiquorum sensing activity in Chromobacterium violaceum was performed by measuring inhibition of quorum sensing dependent violacein production. The centesimal composition (per 100 g of pulp) was as follows: protein 3.68 ± 0.21 g, lipids 0.02 ± 0.03 g, carbohydrates 10.31 g and fiber 2.06 g. Trace elements (mg/g of pulp) were determined as: K 0.90, Ca 3.36, Fe 0.60, Zn 0.17, Cl 0.56, Cr 0.06, Ni 0.04, and Cu 0.07. The pulp is a source of phenolic compounds and presents antioxidant activity similar to other berries. The fruit phenolic extract inhibited all tested bacteria. We also found that the fruit phenolic extract at low subinhibitory concentrations inhibited up to 96% of violacein production in C. violaceum, likely due to the fruit's phenolic content. This study shows the contribution of E. uniflora phenolic compounds to the antioxidant, antimicrobial and the newly discovered quorum quenching activity, all of which could be used by the food and pharmaceutical industries to develop new functional products. © 2016 Institute of Food Technologists®.

Ultrasound-assisted ionic liquid-based micellar extraction combined with microcrystalline cellulose as sorbent in dispersive microextraction for the determination of phenolic compounds in propolis.

PubMed

Cao, Jun; Peng, Li-Qing; Du, Li-Jing; Zhang, Qi-Dong; Xu, Jing-Jing

2017-04-22

An ionic liquid-(IL) based micellar extraction combined with microcrystalline cellulose- (MCC) assisted dispersive micro solid-phase extraction method was developed to extract phenolic compounds from propolis. A total of 20 target compounds were identified by ultra-high- performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. The main extraction parameters were optimized and included the ultrasonic power, ultrasonic time, sample pH, type of IL, the concentration of [C12mim]Br, extraction time, concentration of MCC, type of sorbent and type of elution solvents. Under the optimum conditions, the proposed method exhibited good linearities (r 2  ≥ 0.999) for all plant phenolic compounds with the lower limits of detection in the range of 0.21-0.41 ng/mL. The recoveries ranged from 82.74% to 97.88% for pinocembrin, chrysin and galangin. Compared with conventional solvent extraction, the present method was simpler and more efficient and required less organic solvent and a shorter extraction time. Finally, the methodology was successfully used for the extraction and enrichment of phenolic compounds in propolis. Copyright © 2017 Elsevier B.V. All rights reserved.

Characterization of bioactive compounds in Tunisian bitter orange (Citrus aurantium L.) peel and juice and determination of their antioxidant activities.

PubMed

Jabri Karoui, Iness; Marzouk, Brahim

2013-01-01

Citrus aurantium peel and juice aroma compounds were investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), whereas phenolic compounds analysis was performed by reversed-phase high-performance liquid chromatography (RP-HPLC). Limonene was the major volatile compound of bitter orange peel (90.25%) and juice (91.61%). HPLC analysis of bitter orange peel and juice methanolic extracts indicated that phenolic acids constitute their main phenolic class representing 73.80% and 71.25%, respectively, followed by flavonoids (23.02% and 23.13%, resp.). p-Coumaric and ferulic acids were the most abundant phenolic compounds representing 24.68% and 23.79%, respectively, in the peel, while the juice contained 18.02% and 19.04%, respectively. The antioxidant activities of bitter orange peel and juice methanolic extracts have been evaluated using four in vitro assays, and the results were compared with the standard antioxidants (BHT, BHA, and ascorbic acid). Our findings demonstrated that Citrus aurantium peel and juice possess antioxidant activities which were less effective than those of antioxidant standards. Both extracts may be suggested as a new potential source of natural antioxidant.

Wild Roman chamomile extracts and phenolic compounds: enzymatic assays and molecular modelling studies with VEGFR-2 tyrosine kinase.

PubMed

Guimarães, Rafaela; Calhelha, Ricardo C; Froufe, Hugo J C; Abreu, Rui M V; Carvalho, Ana Maria; Queiroz, Maria João R P; Ferreira, Isabel C F R

2016-01-01

Angiogenesis is a process by which new blood vessels are formed from the pre-existing vasculature, and it is a key process that leads to tumour development. Some studies have recognized phenolic compounds as chemopreventive agents; flavonoids, in particular, seem to suppress the growth of tumor cells modifying the cell cycle. Herein, the antiangiogenic activity of Roman chamomile (Chamaemelum nobile L.) extracts (methanolic extract and infusion) and the main phenolic compounds present (apigenin, apigenin-7-O-glucoside, caffeic acid, chlorogenic acid, luteolin, and luteolin-7-O-glucoside) was evaluated through enzymatic assays using the tyrosine kinase intracellular domain of the Vascular Endothelium Growth Factor Receptor-2 (VEGFR-2), which is a transmembrane receptor expressed fundamentally in endothelial cells involved in angiogenesis, and molecular modelling studies. The methanolic extract showed a lower IC50 value (concentration that provided 50% of VEGFR-2 inhibition) than the infusion, 269 and 301 μg mL(-1), respectively. Regarding phenolic compounds, luteolin and apigenin showed the highest capacity to inhibit the phosphorylation of VEGFR-2, leading us to believe that these compounds are involved in the activity revealed by the methanolic extract.

Bioenergetic strategy of microalgae for the biodegradation of tyrosol and hydroxytyrosol.

PubMed

Papazi, Aikaterini; Ioannou, Andreas; Symeonidi, Myrto; Doulis, Andreas G; Kotzabasis, Kiriakos

2017-05-01

Olive mill wastewater has significant polluting properties due to its high phenolic content [mainly tyrosol (trs) and hydroxytyrosol (htrs)]. Growth kinetics and a series of fluorescence induction measurements for Scenedesmus obliquus cultures showed that microalgae can be tolerant of these phenolic compounds. Changes in the cellular energy reserves and concentration of the phenolic compounds adjust the "toxicity" of these compounds to the microalgae and are, therefore, the main parameters that affect biodegradation. Autotrophic growth conditions of microalgae and high concentrations of trs or htrs induce higher biodegradation compared with mixotrophic conditions and lower phenolic concentrations. When microalgae face trs and htrs simultaneously, biodegradation begins from htrs, the more energetically demanding compound. All these lead to the conviction that microalgae have a "rational" management of cellular energy balance. Low toxicity levels lead to higher growth and lower biodegradation, whereas higher toxicity levels lead to lower growth and higher biodegradation. The selection of appropriate conditions (compatible to the bioenergetic strategies of microalgae) seems to be the key for a successful biodegradation of a series of toxic compounds, thus paving the way for future biotechnological applications for solving complicated pollution problems, like the detoxification of olive mill wastewater.

Characterization of Bioactive Compounds in Tunisian Bitter Orange (Citrus aurantium L.) Peel and Juice and Determination of Their Antioxidant Activities

PubMed Central

Jabri karoui, Iness; Marzouk, Brahim

2013-01-01

Citrus aurantium peel and juice aroma compounds were investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), whereas phenolic compounds analysis was performed by reversed-phase high-performance liquid chromatography (RP-HPLC). Limonene was the major volatile compound of bitter orange peel (90.25%) and juice (91.61%). HPLC analysis of bitter orange peel and juice methanolic extracts indicated that phenolic acids constitute their main phenolic class representing 73.80% and 71.25%, respectively, followed by flavonoids (23.02% and 23.13%, resp.). p-Coumaric and ferulic acids were the most abundant phenolic compounds representing 24.68% and 23.79%, respectively, in the peel, while the juice contained 18.02% and 19.04%, respectively. The antioxidant activities of bitter orange peel and juice methanolic extracts have been evaluated using four in vitro assays, and the results were compared with the standard antioxidants (BHT, BHA, and ascorbic acid). Our findings demonstrated that Citrus aurantium peel and juice possess antioxidant activities which were less effective than those of antioxidant standards. Both extracts may be suggested as a new potential source of natural antioxidant. PMID:23841062

Phenolic Composition and Antioxidant Activity of Malus domestica Leaves

PubMed Central

Viškelis, Pranas; Uselis, Norbertas

2014-01-01

The aim of this study was to determine the composition and content of phenolic compounds in the ethanol extracts of apple leaves and to evaluate the antioxidant activity of these extracts. The total phenolic content was determined spectrophotometrically, as well as the total flavonoid content in the ethanol extracts of apple leaves and the antioxidant activity of these extracts, by the ABTS, DPPH, and FRAP assays. The highest amount of phenolic compounds and flavonoids as well as the highest antioxidant activity was determined in the ethanol extracts obtained from the apple leaves of the cv. Aldas. The analysis by the HPLC method revealed that phloridzin was a predominant component in the ethanol extracts of the apple leaves of all cultivars investigated. The following quercetin glycosides were identified and quantified in the ethanol extracts of apple leaves: hyperoside, isoquercitrin, avicularin, rutin, and quercitrin. Quercitrin was the major compound among quercetin glycosides. PMID:25302319

Antioxidative and antiradical properties of plant phenolics.

PubMed

Sroka, Zbigniew

2005-01-01

The plant phenolic compounds such as flavonoids, tannins and phenolic acids appeared to be strong antiradical and antioxidant compounds. The number of hydroxy groups and the presence of a 2,3-double bond and orthodiphenolic structure enhance antiradical and antioxidative activity of flavonoids. The glycosylation, blocking the 3-OH group in C-ring, lack of a hydroxy group or the presence of only a methoxy group in B-ring have a decreasing effect on antiradical or antioxidative activity of these compounds. Tannins show strong antioxidative properties. Some tannins in red wine or gallate esters were proved to have antioxidative effect in vivo. The number of hydroxy groups connected with the aromatic ring, in ortho or para position relative to each other, enhance antioxidative and antiradical activity of phenolic acids. The substitution of a methoxy group in ortho position to the OH in monophenols seems to favour the antioxidative activity of the former.

Profiling the Phenolic Compounds of the Four Major Seed Coat Types and Their Relation to Color Genes in Lentil.

PubMed

Mirali, Mahla; Purves, Randy W; Vandenberg, Albert

2017-05-26

Phenolic compounds can provide antioxidant health benefits for humans, and foods such as lentils can be valuable dietary sources of different subclasses of these secondary metabolites. This study used LC-MS analyses to compare the phenolic profiles of lentil genotypes with four seed coat background colors (green, gray, tan, and brown) and two cotyledon colors (red and yellow) grown at two locations. The mean area ratio per mg sample (MARS) values of various phenolic compounds in lentil seeds varied with the different seed coat colors conferred by specific genotypes. Seed coats of lentil genotypes with the homozygous recessive tgc allele (green and gray seed coats) had higher MARS values of flavan-3-ols, proanthocyanidins, and some flavonols. This suggests lentils featuring green and gray seed coats might be more promising as health-promoting foods.

Phenolic composition and antioxidant activity of Malus domestica leaves.

PubMed

Liaudanskas, Mindaugas; Viškelis, Pranas; Raudonis, Raimondas; Kviklys, Darius; Uselis, Norbertas; Janulis, Valdimaras

2014-01-01

The aim of this study was to determine the composition and content of phenolic compounds in the ethanol extracts of apple leaves and to evaluate the antioxidant activity of these extracts. The total phenolic content was determined spectrophotometrically, as well as the total flavonoid content in the ethanol extracts of apple leaves and the antioxidant activity of these extracts, by the ABTS, DPPH, and FRAP assays. The highest amount of phenolic compounds and flavonoids as well as the highest antioxidant activity was determined in the ethanol extracts obtained from the apple leaves of the cv. Aldas. The analysis by the HPLC method revealed that phloridzin was a predominant component in the ethanol extracts of the apple leaves of all cultivars investigated. The following quercetin glycosides were identified and quantified in the ethanol extracts of apple leaves: hyperoside, isoquercitrin, avicularin, rutin, and quercitrin. Quercitrin was the major compound among quercetin glycosides.

Optimization of ultrasound extraction of phenolic compounds from coconut (Cocos nucifera) shell powder by response surface methodology.

PubMed

Rodrigues, Sueli; Pinto, Gustavo A S; Fernandes, Fabiano A N

2008-01-01

Coconut is a tropical fruit largely consumed in many countries. In some areas of the Brazilian coast, coconut shell represents more than 60% of the domestic waste volume. The coconut shell is composed mainly of lignin and cellulose, having a chemical composition very similar to wood and suitable for phenolic extraction. In this work, the use of ultrasound to extract phenolic compounds from coconut shell was evaluated. The effect of temperature, solution to solid ratio, pH and extraction time were evaluated through a 2(4) experimental planning. The extraction process was also optimized using surface response methodology. At the optimum operating condition (30 degrees C, solution to solid ratio of 50, 15 min of extraction and pH 6.5) the process yielded 22.44 mg of phenolic compounds per gram of coconut shell.

Metabolic profile of the bioactive compounds of burdock (Arctium lappa) seeds, roots and leaves.

PubMed

Ferracane, Rosalia; Graziani, Giulia; Gallo, Monica; Fogliano, Vincenzo; Ritieni, Alberto

2010-01-20

In this work the bioactive metabolic profile, the antioxidant activity and total phenolic content of burdock (Arctium lappa) seeds, leaves and roots were obtained. TEAC values and total phenolic content for hydro-alcoholic extracts of burdock ranged from 67.39 to 1.63 micromol Trolox equivalent/100g dry weight (DW), and from 2.87 to 45 g of gallic acid equivalent/100g DW, respectively. Phytochemical compounds were analyzed by liquid chromatography coupled to electrospray tandem mass spectrometry (LC/MS/MS) in negative mode. The main compounds of burdock extracts were caffeoylquinic acid derivatives, lignans (mainly arctiin) and various flavonoids. The occurrence of some phenolic acids (caffeic acid, chlorogenic acid and cynarin) in burdock seeds; arctiin, luteolin and quercetin rhamnoside in burdock roots; phenolic acids, quercetin, quercitrin and luteolin in burdock leaves was reported for the first time.

Fruit Antioxidants during Vinegar Processing: Changes in Content and in Vitro Bio-Accessibility

PubMed Central

Bakir, Sena; Toydemir, Gamze; Boyacioglu, Dilek; Beekwilder, Jules; Capanoglu, Esra

2016-01-01

Background: Vinegars based on fruit juices could conserve part of the health-associated compounds present in the fruits. However, in general very limited knowledge exists on the consequences of vinegar-making on different antioxidant compounds from fruit. In this study vinegars derived from apple and grape are studied. Methods: A number of steps, starting from the fermentation of the fruit juices to the formation of the final vinegars, were studied from an industrial vinegar process. The effect of each of the vinegar processing steps on content of antioxidants, phenolic compounds and flavonoids was studied, by spectroscopic methods and by high-performance liquid chromatography (HPLC). Results: The major observation was that spectrophotometric methods indicate a strong loss of antioxidant phenolic compounds during the transition from fruit wine to fruit vinegar. A targeted HPLC analysis indicates that metabolites such as gallic acid are lost in later stages of the vinegar process. Conclusion: The major conclusion of this work is that major changes occur in phenolic compounds during vinegar making. An untargeted metabolite analysis should be used to reveal these changes in more detail. In addition, the effect of vinegar processing on bio-accessibility of phenolic compounds was investigated by mimicking the digestive tract in an in vitro set up. This study is meant to provide insight into the potential of vinegar as a source of health-related compounds from fruit. PMID:27690020

Phenol-Rich Compounds Sweet Gel: A Statistically More Effective Antibiotic than Cloxacillin Against Pseudomonas Aeruginosa.

PubMed

Dashtdar, Mehrab; Dashtdar, Mohammad Reza; Dashtdar, Babak; Khan, Gazala Afreen; Kardi, Karima

2016-09-01

The purpose of this study was to obtain a natural antibiotic from Phenol-rich compounds; for the dressing and the treatment of chronic wounds. The Phenol-rich compound sweet gel was prepared by blending four natural herbal extracts, Acacia catechu (L.F.), Momia ( Shilajit ), Castanea sativa , and Ephedra sinica stapf , with combination of a sweet gel medium, including honey, maple saps, Phoenix dactylifera L . (date), pomegranate extract and Azadirachta indica gum as a stabilizer. The combinations were screened by using a well-diffusion assay with cloxacillin as a control. Pseudomonas spp. was tested with our novel antimicrobial compound. The zones of inhibition in agar culture were measured for each individual component and for the compound, and the results were compared with those of the control group which had been treated with cloxacillin. Data were expressed as means ± standard deviations. Quantitative analyses were performed using the paired t -test. The antibiotic effect of the Phenol-rich compound sweet gel was statistically shown to be more significant than that of cloxacillin against Pseudomonas aeruginosa ( P < 0.05). Our novel approach to fighting the antibiotic resistance of Pseudomonas proved to be successful. The Phenol-rich compound sweet gel was found to be suitable for use as an alternative medicine and bioactive dressing material, for the treatment of patients with various types of wounds, including burns, venous leg ulcers, ulcers of various etiologies, leg ulcers on the feet of diabetic, unhealed graft sampling sites, abscesses, boils, surgical wounds, necrotic process, post-operative and neonatal wound infection, and should be considered as an alternative to the usual methods of cure.

Phenol-Rich Compounds Sweet Gel: A Statistically More Effective Antibiotic than Cloxacillin Against Pseudomonas Aeruginosa

PubMed Central

Dashtdar, Mehrab; Dashtdar, Mohammad Reza; Dashtdar, Babak; Khan, Gazala Afreen; Kardi, Karima

2016-01-01

Objectives: The purpose of this study was to obtain a natural antibiotic from Phenol-rich compounds; for the dressing and the treatment of chronic wounds. Methods: The Phenol-rich compound sweet gel was prepared by blending four natural herbal extracts, Acacia catechu (L.F.), Momia (Shilajit), Castanea sativa, and Ephedra sinica stapf, with combination of a sweet gel medium, including honey, maple saps, Phoenix dactylifera L. (date), pomegranate extract and Azadirachta indica gum as a stabilizer. The combinations were screened by using a well-diffusion assay with cloxacillin as a control. Pseudomonas spp. was tested with our novel antimicrobial compound. The zones of inhibition in agar culture were measured for each individual component and for the compound, and the results were compared with those of the control group which had been treated with cloxacillin. Data were expressed as means ± standard deviations. Quantitative analyses were performed using the paired t-test. Results: The antibiotic effect of the Phenol-rich compound sweet gel was statistically shown to be more significant than that of cloxacillin against Pseudomonas aeruginosa (P < 0.05). Conclusion: Our novel approach to fighting the antibiotic resistance of Pseudomonas proved to be successful. The Phenol-rich compound sweet gel was found to be suitable for use as an alternative medicine and bioactive dressing material, for the treatment of patients with various types of wounds, including burns, venous leg ulcers, ulcers of various etiologies, leg ulcers on the feet of diabetic, unhealed graft sampling sites, abscesses, boils, surgical wounds, necrotic process, post-operative and neonatal wound infection, and should be considered as an alternative to the usual methods of cure. PMID:27695634

Foliar phenolic compounds of ten wild species of Verbenacea as antioxidants and specific chemomarkers.

PubMed

Ávila-Reyes, J A; Almaraz-Abarca, N; Chaidez-Ayala, A I; Ramírez-Noya, D; Delgado-Alvarado, E A; Torres-Ricario, R; Naranjo-Jiménez, N; Alanís-Bañuelos, R E

2018-02-01

The family Verbenaceae hosts important species used in traditional medicine of many countries. The taxonomic controversies concerning the specific delimitation of several of its species make it difficult to guarantee the botanical origin of herbal preparations based on species of this family. To contribute to the development of both specific chemomarkers and a quality control tool to authenticate the botanical origin of herbal preparations of Verbenacea species, we determined the foliar HPLC-DAD phenolic profiles and the antioxidant properties of 10 wild species of this family occurring in Mexico. The contents of phenols and flavonoids varied significantly among species. Priva mexicana showed the highest levels of total phenolics (53.4 mg g-1 dry tissue) and Verbena carolina had the highest levels of flavonoids (17.89 mg g-1 dry tissue). Relevant antioxidant properties revealed by antiradical and reducing power were found for the analyzed species. These properties varied significantly in a species-dependent manner. The phenolic compounds accumulated were flavones and phenolic acids. Flavones were the only type of flavonoids found. The results of a cluster analysis showed that the compounds were accumulated in species-specific profiles. The phenolic profiles are proposed as valuable chemomarkers that can become a useful tool for the quality control concerning the botanical origin of herbal medicinal preparations based on the species analyzed. In addition, phenolic profiles could contribute importantly to solve the taxonomic controversies concerning species delimitation in the family Verbenaceae.

Bactericidal activity of glutaraldehyde-like compounds from olive products.

PubMed

Medina, Eduardo; Brenes, Manuel; García, Aranzazu; Romero, Concepción; de Castro, Antonio

2009-12-01

The bactericidal effects of several olive compounds (nonenal, oleuropein, tyrosol, the dialdehydic form of decarboxymethyl elenolic acid either free [EDA] or linked to tyrosol [TyEDA] or to hydroxytyrosol [HyEDA]), other food phenolic compounds (catechin, epicatechin, eugenol, thymol, carvacrol, and carnosic acid), and commercial disinfectants (glutaraldehyde [GTA] and ortho-phthalaldehyde [OPA]), were tested against strains of Pseudomonas fluorescens, Staphylococcus aureus, Enterococcus faecalis, and Escherichia coli. It was found that the bactericidal activities of olive GTA-like compounds (EDA, HyEDA, and TyEDA) were greater than those exerted by several food phenolic substances. Surprisingly, these olive antimicrobials were as active as the synthetic biocides GTA and OPA against the four bacteria studied. Thus, it has been proposed that the bactericidal activity of the main olive antimicrobials is primarily due to their dialdehydic structure, which is similar to that of the commercial biocides GTA and OPA. Our results clearly reveal that olive GTA-like compounds possess a strong bactericidal activity even greater than that of other food phenolic compounds or synthetic biocides.

Bioactive compounds and antioxidant activity in scalded Jalapeño pepper industrial byproduct (Capsicum annuum).

PubMed

Sandoval-Castro, Claudia Jaqueline; Valdez-Morales, Maribel; Oomah, B Dave; Gutiérrez-Dorado, Roberto; Medina-Godoy, Sergio; Espinosa-Alonso, L Gabriela

2017-06-01

Bioactive compounds and antioxidant activity were evaluated from industrial Jalapeño pepper byproducts and simulated non processed byproducts from two Mexican states (Chihuahua and Sinaloa) to determine their value added potential as commercial food ingredients. Aqueous 80% ethanol produced about 13% of dry extract of polar compounds. Total phenolic content increased and capsaicin and dihydrocapsaicin decreased on scalding samples (80 °C, 2 min) without affecting ascorbic acid. The major phenolic compounds, rutin, epicatechin and catechin comprised 90% of the total compounds detected by HPLC of each Jalapeño pepper byproducts. ORAC analysis showed that the origin and scalding process affected the antioxidant activity which correlated strongly with capsaicin content. Although scalding decreased capsaicinoids (up to 42%), phenolic content by (up to 16%), and the antioxidant activity (variable). Jalapeño pepper byproduct is a good source of compounds with antioxidant activity, and still an attractive ingredient to develop useful innovative products with potential food/non-food applications simultaneously reducing food loss and waste.

Feasibility in multispectral imaging for predicting the content of bioactive compounds in intact tomato fruit.

PubMed

Liu, Changhong; Liu, Wei; Chen, Wei; Yang, Jianbo; Zheng, Lei

2015-04-15

Tomato is an important health-stimulating fruit because of the antioxidant properties of its main bioactive compounds, dominantly lycopene and phenolic compounds. Nowadays, product differentiation in the fruit market requires an accurate evaluation of these value-added compounds. An experiment was conducted to simultaneously and non-destructively measure lycopene and phenolic compounds content in intact tomatoes using multispectral imaging combined with chemometric methods. Partial least squares (PLS), least squares-support vector machines (LS-SVM) and back propagation neural network (BPNN) were applied to develop quantitative models. Compared with PLS and LS-SVM, BPNN model considerably improved the performance with coefficient of determination in prediction (RP(2))=0.938 and 0.965, residual predictive deviation (RPD)=4.590 and 9.335 for lycopene and total phenolics content prediction, respectively. It is concluded that multispectral imaging is an attractive alternative to the standard methods for determination of bioactive compounds content in intact tomatoes, providing a useful platform for infield fruit sorting/grading. Copyright © 2014 Elsevier Ltd. All rights reserved.