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Protocatechuic Acid (protocatechuic + acid)
Selected AbstractsPhenolic acids in black raspberry and in the gastrointestinal tract of pigs following ingestion of black raspberryMOLECULAR NUTRITION & FOOD RESEARCH (FORMERLY NAHRUNG/FOOD), Issue S1 2009Xianli Wu Abstract Black raspberries (BRB) contain high levels of polyphenols and have been demonstrated to be chemopreventive. In order to investigate the underlying mechanism and study the metabolism of anthocyanins, pigs were fed freeze-dried BRB powder or purified diet (control) and three segments of the gastrointestinal (GI) tract (small intestine, cecum, and colon; 4 h after feeding) were collected for analysis of phenolic acids. Protocatechuic acid was the major phenolic acid (8.35 mg/100 g, dry weight (DW)) in BRB, followed by p -coumaric acid (1.63 mg/100 g, DW), caffeic acid (1.34 mg/100 g, DW), ferulic acid (0.24 mg/100 g, DW), and 3-hydroxybenzoic acid (0.20 mg/100 g, DW). Recoveries of these five phenolic acids in the whole GI tract were 199.9 ± 54.0%, 7.0 ± 3.0%, 37.0 ± 9.7%, 56.6 ± 31.3%, and 916.8 ± 642.3% (mean ± SEM, n = 5), respectively, and quantities in contents of the GI tract ranged from 0.13 ± 0.05 ,mol (p -coumaric acid) to 23.47 ± 6.09 ,mol (protocatechuic acid) (mean ± SEM, n = 5). Six other phenolic acids were detected primarily in the cecum and/or colon which were not in BRB, with total contents in the GI tract ranging from 0.18 ± 0.18 ,mol (homovanillic acid) to 8.49 ± 4.31 ,mol (homoprotocatechuic acid). Total phenolic acids in the GI tract were 49.32 ± 16.37 ,mol (mean ± SEM, n = 5). Phenolic acids measured in the GI tract accounted for only 6.31% of the degraded anthocyanins. [source] Inhibition of lipid peroxidation by anthocyanins, anthocyanidins and their phenolic degradation productsEUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, Issue 1 2007Jonathan E. Brown Abstract Food components that delay or prevent biomolecule oxidation may be relevant in shelf life extension as well as disease prevention. Anthocyanins are a potentially important group of compounds, but they are prone to degradation both in vitro and in vivo, producing simple phenols. In this study, eight structurally related (poly)phenols [anthocyan(id)ins and phenolic acids] were examined for their ability to inhibit lipid oxidation at physiologically relevant concentrations (100,1000,nM) using the Cu2+ -mediated low-density lipoprotein oxidation model. Interaction between each (poly)phenol and Cu2+ ions was also investigated. (Poly)phenols with an ortho -dihydroxy group arrangement, i.e. cyanidin-3-glucoside, cyanidin and protocatechuic acid, were the most effective within their class, extending the lag phase to oxidation by 137, 255 and 402%, respectively (at 1000,nM). At the same concentration, trihydroxy-substituted compounds (delphinidin and gallic acid) were of intermediate efficacy, extending the lag phase by 175 and 38%, respectively. Compounds with the 4'-hydroxy-3',5'-methoxy arrangement (i.e. malvidin-3-glucoside and malvidin) were the least effective (3 and 58% extension, respectively), while syringic acid (4-hydroxy-3,5-dihydroxy benzoic acid) was pro-oxidant (lag phase shortened by 31%). (Poly)phenols with the ortho -dihydroxy arrangement chelated Cu2+ ions, which in part explains their greater efficacy over the other (poly)phenols in this model oxidation system. However, differences in their hydrogen-donating properties and their partitioning between lipid and hydrophilic phases are also relevant in explaining these structure-activity relationships. [source] The effect of nitrogen fertilization on fungistatic phenolic compounds in roots of beech (Fagus sylvatica) and Norway spruce (Picea abies)FOREST PATHOLOGY, Issue 4 2005L. Tomova Summary The effect of nitrogen fertilization on fungistatic phenolic compounds in fine roots of beech and Norway spruce growing in afforestation plots was analysed. The plots were situated at two sites in Switzerland on acidic soil with low base saturation. For 9 years, the trees have been treated with dry ammonium nitrate to give 0, 10, 20, 40, 80, 160 kg N ha,1 year,1, respectively. The phenolic compounds responded differently to fertilization. Fine roots of beech showed a significant decrease of (,)-epicatechin and piceatannol with increasing nitrogen fertilization. The concentration of protocatechuic acid was increased with fertilization. Roots of fertilized Norway spruce showed significantly decreased concentrations of 4-hydroxyacetophenone and piceatannol. The mycelial growth of three isolates each of Heterobasidion annosum s.l. and Cylindrocarpon destructans was tested on agar media containing various phenolic compounds in concentrations found in fine roots of Norway spruce (Picea abies) and beech (Fagus sylvatica). All three H. annosum isolates were inhibited by p-coumaric acid and (,)-epicatechin. Two isolates were inhibited by another four phenolic compounds (p-hydroxybenzoic acid, 4-hydroxyacetophenone, piceatannol and protocatechuic acid), one by (+)-catechin. Two of three C. destructans isolates were inhibited by all phenolic compounds except for (+)-catechin which affected only one isolate, one isolate did not respond at all. Résumé L'effet d'une fertilisation azotée sur les composés phénoliques fongistatiques des racines fines de Hêtre (Fagus sylvatica) et d'Epicea (Picea abies) a été analysé dans des parcelles de reboisement. Ces parcelles sont situées dans deux localités de Suisse sur sol acide, avec un faible taux de saturation en bases. Pendant neuf ans, les arbres ont été traités par apports secs de nitrate d'ammonium à raison de 0, 10, 20, 40, 80, 160 kg N par hectare et par an, respectivement. La réponse des composés phénoliques à la fertilisation est variable. Les racines fines de hêtres ont montré une baisse significative d'épicatèchine (,) et de piceatannol avec l'augmentation de la fertilisation azotée. Les concentrations d'acide protocatéchique ont augmenté avec la fertilisation. Les racines d'épicèas fertilisés ont montré une baisse significative des concentrations de 4-hydroxyacétophénone et de piceatannol. La croissance mycélienne de trois isolats de chacune des espèces H .annosum s.l. et Cylindrocarpon destructans a été testée sur milieu agar contenant les différents composés phénoliques aux concentrations trouvées dans les racines fines d'épicèas (Picea abies) et de hêtres (Fagus sylvatica). Les trois isolats d'Heterobasidion annosum s.l. ont été inhibés par l'acide p-coumarique et l'épicatèchine (,). Deux isolats ont été inhibés par quatre autres composés phénoliques (acide p-hydroxybenzoïque, 4-hydroxyacétophénone, piceatannol et acide protocatéchique) et un par la catéchine (+). Deux des trois isolats de Cylindrocarpon destructans ont été inhibés par tous les composés phénoliques à l'exception de la catéchine (+) pour l'un des deux, le dernier isolat ne répondant à aucun composé. Zusammenfassung In einer Aufforstungs-Versuchsfläche wurde der Einfluss einer Stickstoffdüngung auf die fungistatischen phenolischen Verbindungen in Feinwurzeln von jungen Buchen und Fichten untersucht. Die Versuchsflächen befanden sich an zwei Standorten in der Schweiz mit sauren, basenarmen Bodenverhältnissen. Die Bäume wurden über neun Jahre mit 0, 10, 20, 40, 80 und 160 kg N ha,1 a,1 in Form von Ammoniumnitrat gedüngt. Die phenolischen Verbindungen reagierten unterschiedlich auf die Düngung. Die Feinwurzeln von Buchen zeigten mit zunehmender Stickstoffdüngung eine signifikante Abnahme von (,) Epicatechin und Piceatannol, während die Konzentration von Protocatechinsäure durch die Düngung erhöht wurde. Die Feinwurzeln gedüngter Fichten wiesen ebenfalls signifikant tiefere Konzentrationen von 4-Hydroyacetophenon und Piceatannol auf. In in-vitro-Tests wurde das Myzelwachstum von allen drei geprüften Isolaten von Heterobasidion annosum s. l. durch die in den Wurzeln gefundenen Konzentrationen von p-Coumarinsäure und (,)Epicatechin gehemmt. Zwei Pilzisolate zeigten zudem eine Hemmung durch vier weitere in den Wurzeln gefundene phenolische Verbindungen, nämlich p-Hydroxybenzoesäure, 4-Hydroxyacetophenon, Piceatannol und Protocatechinsäure, und eines wurde auch durch (+)-Catechin gehemmt. Bei zwei von drei geprüften Isolaten von Cylindrocarpon destructans wurde das Myzelwachstum durch alle untersuchten phenolischen Verbindungen gehemmt, mit Ausnahme von (+)-Catechin, welches sich nur auf ein Isolat negativ auswirkte. Ein Isolat von C. destructans reagierte auf keine der genannten Substanzen. [source] Determination of some hydroxybenzoic acids and catechins in white wine samples by liquid chromatography with luminescence detectionJOURNAL OF SEPARATION SCIENCE, JSS, Issue 18 2006Rafael Carlos Rodríguez-Díaz Abstract A liquid chromatographic method with luminescence detection for the determination of eight phenolic compounds is reported. The method involves postcolumn derivatization with terbium(III). This derivatization is based on the reaction between phenolics and terbium(III) to form luminescent chelates, which were determined at ,ex 295 and ,em 545 nm using the fluorescence mode. The long wavelength emission of lanthanide chelates can minimize interferences from background sample matrix, which usually emit at shorter wavelengths. Also, the chromatographic separation allows the individual determination of phenolics, which cannot be done using the direct measurement of the fluorescence of their corresponding terbium chelates. Dynamic ranges of the calibration graphs and detection limits, obtained with standard solutions of analytes were (,g/mL): gallic acid (0.9,40, 0.3), protocatechuic acid (0.05,7, 0.016), catechin (0.2,40, 0.07), vanillic acid (0.25,40, 0.08), p -hydroxybenzoic acid (0.8,40, 0.25), syringic acid (0.17,40, 0.05), epicatechin (0.3,40, 0.09) and salicylic acid (0.07,12, 0.02). The precision was established at two concentration levels of each analyte and expressed as the percentage of RSD with values ranging between 1.0 and 6.5%. The practical usefulness of the method was demonstrated by the analysis of white wine samples, which were diluted two-fold and directly injected into the chromatographic system. The recovery values obtained ranged between 93.3 and 108.0%. [source] Phenolic compounds in some apple (Malus domestica Borkh) cultivars of organic and integrated productionJOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, Issue 10 2005Robert Veberic Abstract Eleven organically grown apple cultivars and 11 apple cultivars of integrated production from Austria and Slovenia were analyzed by HPLC for the content of phenolic compounds in peel and pulp. We identified chlorogenic acid, p -coumaric acid, procyanidin B3, protocatechuic acid, (,)-epicatechin, phloridzin, rutin and quercetin-3-rhamnoside in apple peel. In apple pulp, (+)-catechin was also identified in all the cultivars. Some other phenols (procyanidin B3, rutin and quercetin-3-rhamnoside) could not be identified or were not properly separated. With regard to the phenolic content in the apple peel, there were no differences between organically grown apple cultivars and apple cultivars of integrated production. Organically grown apples, however, exhibited a higher content of phenolic substances in the apple pulp compared with the apple cultivars of integrated production. This may be due either to the different genotype source or to the growing technology. Higher concentrations of phenolic compounds in organically grown cultivars could be a result of plant response to stress. The apple peel contained higher concentrations of identified phenols than the pulp. The apple peel represents up to 10% of the whole fruit; therefore the phenolsic compounds in the pulp are of greater importance to the consumer than the phenolic compounds in the peel. Copyright © 2005 Society of Chemical Industry [source] Chemiluminescence determination of pharmacologically active compounds by capillary electrophoresisLUMINESCENCE: THE JOURNAL OF BIOLOGICAL AND CHEMICAL LUMINESCENCE, Issue 6 2005Suqin Han Abstract A simple and rapid capillary electrophoresis with direct chemiluminescence method has been developed for the determination of five natural pharmacologically active compounds including rutin, protocatechuic aldehyde, chlorogenic acid, luteolin and protocatechuic acid. The luminol as a component of the separation electrolyte buffer was introduced at the head of the separation capillary. The separation of five compounds was carried out in a fused-silica capillary with 15.0 mmol/L tetraborate, 1.0 mmol/L SDS and 0.42 mmol/L luminol (pH 8.5). The analytes was determined by enhancing the chemiluminescence of luminol with 0.13 mmol/L K3Fe(CN)6 in 0.05 mol/L NaOH, which was introduced at the post-column stage. The voltage applied was 16 kV. Under the optimum conditions, the analytes were separated within 10 min. The excellent linearity was obtained over two to three orders of magnitude with a detection limit (signal:noise = 3) of 0.012,0.055 µmol/L for all five analytes. The method was successfully used in the analysis of pharmaceutical and biological samples, and the assay results were satisfactory. Copyright © 2005 John Wiley & Sons, Ltd. [source] Phenolic acids in black raspberry and in the gastrointestinal tract of pigs following ingestion of black raspberryMOLECULAR NUTRITION & FOOD RESEARCH (FORMERLY NAHRUNG/FOOD), Issue S1 2009Xianli Wu Abstract Black raspberries (BRB) contain high levels of polyphenols and have been demonstrated to be chemopreventive. In order to investigate the underlying mechanism and study the metabolism of anthocyanins, pigs were fed freeze-dried BRB powder or purified diet (control) and three segments of the gastrointestinal (GI) tract (small intestine, cecum, and colon; 4 h after feeding) were collected for analysis of phenolic acids. Protocatechuic acid was the major phenolic acid (8.35 mg/100 g, dry weight (DW)) in BRB, followed by p -coumaric acid (1.63 mg/100 g, DW), caffeic acid (1.34 mg/100 g, DW), ferulic acid (0.24 mg/100 g, DW), and 3-hydroxybenzoic acid (0.20 mg/100 g, DW). Recoveries of these five phenolic acids in the whole GI tract were 199.9 ± 54.0%, 7.0 ± 3.0%, 37.0 ± 9.7%, 56.6 ± 31.3%, and 916.8 ± 642.3% (mean ± SEM, n = 5), respectively, and quantities in contents of the GI tract ranged from 0.13 ± 0.05 ,mol (p -coumaric acid) to 23.47 ± 6.09 ,mol (protocatechuic acid) (mean ± SEM, n = 5). Six other phenolic acids were detected primarily in the cecum and/or colon which were not in BRB, with total contents in the GI tract ranging from 0.18 ± 0.18 ,mol (homovanillic acid) to 8.49 ± 4.31 ,mol (homoprotocatechuic acid). Total phenolic acids in the GI tract were 49.32 ± 16.37 ,mol (mean ± SEM, n = 5). Phenolic acids measured in the GI tract accounted for only 6.31% of the degraded anthocyanins. [source] Fungitoxic phenols from carnation (Dianthus caryophyllus) effective against Fusarium oxysporum f. sp. dianthiPHYTOCHEMICAL ANALYSIS, Issue 1 2003Paolo Curir Abstract The phenol compositions of two cultivars of carnation (Dianthus caryophyllus) namely "Gloriana" and "Roland", which are partially and highly resistant, respectively, to Fusarium oxysporum f. sp. dianthi have been investigated with the aim of determining if endogenous phenols could have an anti-fungal effect against the pathogen. Analyses were performed on healthy and F. oxysporum -inoculated in vitro tissues, and on in vivo plants. Two benzoic acid derivatives, protocatechuic acid (3,4-dihydroxybenzoic acid) and vanillic acid (4-hydroxy-3-methoxybenzoic acid), were found within healthy and inoculated tissues of both cultivars, together with the flavonol glycoside peltatoside (3-[6-O-(,- L -arabinopyranosyl)-,- D -glucopyranosyl] quercetin). These molecules proved to be only slightly inhibitory towards the pathogen. 2,6-Dimethoxybenzoic acid was detected in small amounts only in the inoculated cultivar "Gloriana", while the highly resistant cultivar "Roland" showed the presence of the flavone datiscetin (3,5,7,2,-tetrahydroxyflavone). The latter compound exhibited an appreciable fungitoxic activity towards F. oxysporum f. sp. dianthi. Copyright © 2003 John Wiley & Sons, Ltd. [source] Determination of Bioactive Components in Polygonum perfoliatum L. by Capillary Electrophoresis with Electrochemical DetectionCHINESE JOURNAL OF CHEMISTRY, Issue 4 2009Shuping JIN Abstract The major bioactive components in a Chinese herb named Polygonum perfoliatum L. including ferulic acid, vanillic acid, quercetin, caffeic acid and protocatechuic acid were simultaneously determined by capillary electrophoresis with electrochemical detection (CE-ED) in this paper. The effects of working electrode potential, pH and concentration of running buffer, separation voltage, and injection time on CE-ED were investigated. Under the optimum conditions, the five analytes could be separated within 17 min at a separation voltage of 18 kV in 10 mmol· L,1 phosphate buffer (pH 9.2). A 300 µm diameter carbon disk electrode generated good responses at +0.95 V (vs. SCE) to the five analytes. The response was linear over three orders of magnitude with detection limits (S/N=3) ranging from 7.1×10,8 to 9.3×10,8 g·mL,1 for the analytes. This proposed method could be successfully applied to the analysis of the real samples with relatively simple extraction procedures and satisfactory results. [source] | |||||||||||||