Identification and quantification of low molecular weight phenolic antioxidants in seeds of evening primrose (Oenothera biennis L.)

Crude extracts of evening primrose meal were prepared in 56% (v/v) acetone and separated into six fractions (I-VI) using a Sephadex LH-20 column. Qualitative tests for phenolic and vanillin positive compounds produced positive results for all fractions. Silica gel thin-layer chromatography of fractions III and V allowed the location and isolation of two spots containing moderate to strong antioxidative compounds. High-performance liquid chromatography of the spot isolated from fraction III showed the resolution of two structurally related compounds, whereas that of the spot from fraction V showed the presence of one compound. Nuclear magnetic resonance spectroscopy and electron impact mass spectrometry produced sufficient evidence to identify the isolated compounds as (+)-catechin, (-)-epicatechin, and gallic acid. These compounds accounted for about 10.5 and 1.7% of the dry mass of the crude extracts and meal, respectively.     

Chemical composition and content of antinutritional factors in Polish cultivars of peas

The seeds of 15 Polish pea varieties contained from 221 to 281 g/kg crude protein with a mean of 240.2±3.5 g/kg dry matter (DM). The weight of 1000 pea seeds, depending on cultivar, ranged from 209.4 to 280.4 g. No interactive effect between the seed mass and the crude protein content was detected. The highest significant negative correlation between weight of seeds and dietary fiber content wasr=−0.815^XX. The content of dietary fiber ranged from 161.5 to 209.9 g/kg with a mean of 187.9±3.8 g/kg. The mean gross energy of seeds was 18.1±0.28 MJ/kg. Amino acid composition of all the cultivars was similar, which was indicated by a similar index of essential amino acids (EAAI) of about 69.7±0.25. Trypsin inhibitor content in seeds was from 2.83 to 7.32 TIU/mg and the content of phytates ranged from 6.32 to 13.36 mg/g DM. The mean content of polyphenols and flavanols in analysed pea cultivars was 0.92 amd 0.46 mg/g, respectively. In the seeds of most cultivars little or no pyrimidine glucosides, i.e. vicine and convicine, were found. The overall mean oligosaccharide content was 64.3±1.8 g/kg, of which α-galactosides were 46.8±2.0 g/kg. The antinutritional factor content was not significantly correlated with protein content. No statistical relationship was found between crude protein and dietary fiber content. It was observed that pea cultivars with higher trypsin inhibitor activity contained significantly less flavanols (r=−0.607^X) and α-galactosides (r=−0.617^X). The varieties with higher seed content of dietary fiber contained the highest amount of α-galactosides (r=0.514^X).     

Erratum to: Antioxidant Properties of Extracts Obtained from Raw, Dry-roasted, and Oil-roasted US Peanuts of Commercial Importance

Raw, skinless peanut kernels from US commercial production lines were dry- and oil-roasted according to standard industrial practices. Eighty percent (v/v) methanolic extracts from the peanut cultivars were prepared and characterized by RP-HPLC: five predominant compounds were found comprising free p-coumaric acid and potential p-coumaric acid derivatives, as elucidated by DAD-UV spectra with comparisons to those of commercial standards. A Spanish high-oleic peanut possessed the greatest naturally-occurring level of p-coumaric acid and its derivatives, followed by a high-oleic Runner, a normal Runner, and a Virginia peanut. Upon thermal processing, p-coumaric acid was liberated at the expense of its derivatives according to the relationship: oil roasting > dry roasting > raw. A high-oleic Runner exhibited the greatest increase (∼785%) in free p-coumaric acid levels after oil roasting. For many of the samples from the 2007 crop, processing increased the TPC and antioxidant capacities in the order of raw < dry roast < oil roast, but results were cultivar dependent. Oil-roasted peanuts were more effective at scavenging O₂ ^●- than their dry-roasted counterparts, as determined by a photochemiluminescence assay. Overall findings indicate that although thermal processing altered the composition of peanut kernel antioxidants, TPC values and radical-scavenging activities are preserved. Depending on peanut type, cultivar, and harvest date, enhanced antioxidant capacities can result.     

Antioxidant and antiradical activities in extracts of hazelnut kernel (Corylus avellana L.) and hazelnut green leafy cover

Phenolic compounds in the aqueous systems were extracted, from hazelnut kernel (HK) and hazelnut green leafy cover (HGLC), with 80% (v/v) ethanol (HKe and HGLCe) or 80% (v/v) acetone (HKa and HGLCa). The extracts were examined for their phenolic and condensed tannin contents and phenolic acid profiles (free and esterified fractions) as well as antioxidant and antiradical activities by total antioxidant activity (TAA), antioxidant activity in a beta-carotene-linoleate model system, scavenging of DPPH (2,2-diphenyl-1-picrylhydrazyl) radical, and reducing power. Significant differences (p < 0.05) in the contents of total phenolics, condensed tannins, and TAA existed among the extracts that were examined. HGLCa extract had the highest content of total phenolics (201 mg of catechin equivalents/g of extract), condensed tannins (542 mg of catechin equivalents/g of extract), and TAA (1.29 mmol of Trolox equivalents/g of extract) followed by HGLCe, HKa, and HKe extracts, respectively. Five phenolic acids (gallic acid, caffeic acid, p-coumaric acid, ferulic acid, and sinapic acid) were tentatively identified and quantified, among which gallic acid was the most abundant in both free and esterified forms. The order of antioxidant activity in a beta-carotene-linoleate model system, the scavenging effect on DPPH radical, and the reducing power in all extracts were in the following order: HGLCa > HGLCe > HKa > HKe. These results suggest that both 80% ethanol and acetone are capable of extracting phenolics, but 80% acetone was a more effective solvent for the extraction process. HGLC exhibited stronger antioxidant and antiradical activities than HK itself in both extracts and could potentially be considered as an inexpensive source of natural antioxidants.     

Antioxidant contents and antioxidative properties of traditional rye breads

The purpose of this research was to find out the effect of flour extraction rate on the antioxidative properties of traditional rye bread and then to compare the bioactive compounds content and antioxidant properties of rye breads with commercial wheat roll. Four types of rye flour with different extraction rates of 100 (whole meal dark flour), 95 (brown flour), 90 (brown flour), and 70% (light flour) originated from Warko rye cultivar were used for traditional bread baking with sourdough fermentation. Four types of the respective rye breads were analyzed for their potentially beneficial components, including tocopherols and tocotrienols, total phenolics and flavonoids, reduced glutathione, and inositol hexaphosphates. Moreover, the phenolic acids profile was provided. The Trolox equivalent antioxidant capacity (TEAC) of the breads was evaluated using free radical scavenging activities of 80% methanol extracts against ABTS*+ radical cation (ABTS radical cation decolorization method) whereas radical scavenging activity (RSA) was determined against 2,2-diphenyl-1-picrylhydrazyl radical (DPPH*). The superoxide dismutase-like activity (SOD-like activity) was evaluated as free radical scavenging activities of PBS extracts against superoxide anion radicals (O2*-). The results were compared to whole meal rye bread as well as to wheat roll taken as representative example of wheat based bakery product. The studies showed that flour extraction rates strongly affected the content of bioactive compounds and antioxidative properties of traditionally baked rye breads. The incorporation of the rye flours with extraction rates from 100 down to 70% in the formulation caused decrease in tocopherol (T), tocotrienol (T3), inositol hexaphosphate (IP6), and phenolic compound (TPC) contents in rye breads. No changes in reduced glutathione (GSH) contents were noted between each type of rye bread. A significant decrease in Trolox equivalent antioxidant capacity and radical DDPH scavenging activity was also found in bread formulated on flour with an extraction rate of 70% in comparison to the breads formulated on flour with extraction rates from 100 to 90%. The highest SOD-like activity was noted for rye bread formulated on flour with an extraction rate of 70%. The four types of rye breads showed better antioxidative properties and higher antioxidant contents when compared to wheat roll with one exception made to tocopherols and tocotrienols.     

Nutrient distribution and phenolic antioxidants in air-classified fractions of beach pea (Lathyrus maritimus L.)

Beach pea (Lathyrus maritimus L.) cotyledons and hulls were air-classified into different fractions. The crude protein content (%N x 6.25) of samples ranged from 32.8 to 35.3% in cotyledons and 14.7 to 16.8% in hulls. Crude fiber content was higher in hulls fraction 1 (37.13%) and fraction 2 (36.85%) than in cotyledons (2.83, 2.99, and 3.08% in fractions 1, 2, and 3, respectively). Condensed tannins of cotyledons ranged from 5.76 to 6.90% and of hulls ranged from 52.49 to 57.24%, expressed as catechin equivalents. Minerals, namely P, K, and Zn, were higher in cotyledons, but Ca and Mn were more prevalent in hulls. Nonprotein nitrogen was concentrated in hulls, whereas phytic acid was more abundant in the cotyledons. The UV absorption pattern showed that flavonoids were present in fractions (I-III) from hulls separated on Sephadex LH-20. Fraction III from hulls had the highest content of total phenolics and condensed tannins, but no condensed tannins were detected in fractions I and II from hulls. The antioxidant activity of fractions separated on Sephadex LH-20 from hulls and crude extracts in a beta-carotene-linoleate model system was in the order of fraction III > crude extract > fraction II > fraction I. Spots on silica gel TLC plates, sprayed with a solution of beta-carotene and linoleic acid, indicated that many of the individual compounds were antioxidative in nature. Further, separation of fraction III from hulls on a semipreparative HPLC showed the presence of (+) catechin and (-) epicatechin as the main low-molecular-weight phenolic compounds present.     

Pleiotropic effect of phenolic compounds content increases in transgenic flax plant

The principal goal of this paper was to generate flax (Linum usitatissimum L.) plants with increased antioxidant properties. To accomplish this a vector containing a multigene construct was prepared, and transgenic plants overexpressing essential flavonoid biosynthesis pathway enzymes were generated and analyzed. The simultaneous expression of genes encoding chalcone synthase (CHS), chalcone isomerase (CHI), and dihydroflavonol reductase (DFR) resulted in a significant increase of flax antioxidant capacity. To investigate the determinants of higher antioxidant properties of transgenic plants, the phenolic acids and lignans compound contents were measured. In both green part and seed extracts from transgenic plants, the phenolic acids level was increased when compared to the control. The calculated correlation coefficient between phenolic acids content and antioxidant capacity (0.82 and 0.70 for green part and flaxseed, respectively) perfectly reflects their strong relationship. The increase in yield of transgenic plants and their higher resistance to Fusarium culmorum and Fusarium oxysporum when compared to the control plants was a characteristic feature. It was assessed a very high correlation (correlation coefficient = 0.9) between phenolic acids level in flaxseed extract and resistance to F. culmorum. The flowering date of transgenic plants was approximately 3 weeks earlier than that of the control plants. Interestingly, a significant increase in monounsaturated fatty acids and a slight increase in lignans content accompanied the increase in antioxidant properties of flaxseeds.     

Presence of Caffeic Acid in Flaxseed Lignan Macromolecule

Phenolic compounds were extracted from defatted flaxseeds using ethanol-dioxane (1:1, v/v). The crude extract obtained was purified using Amberlite XAD-16 column chromatography with water and methanol as mobile phases. RP-HPLC and SE-HPLC showed a lignan macromolecule (LM) as a dominant phenolic compound in the purified extract. After the alkaline hydrolysis of LM caffeic acid glucoside (CaAG) was isolated using a semi-preparative HPLC and its structure was confirmed by LC-ESI-MS. In LM of the investigated flaxseed, one molecule of caffeic acid corresponded with five molecules of p-coumaric acid and two molecules of ferulic acid. The presence of caffeic acid in the lignan molecule might be very beneficial due to its high antioxidant activity.     

Antioxidative and radical scavenging effects of phenolics from Vicia sativum

An acetone extract of Vicia sativum seeds and fractions, comprising low molecular-weight phenolics and tannins, displayed good antioxidant activity.     

Antioxidant activity of various fractions of non-tannin phenolics of canola hulls

Cyclone canola hulls were extracted with 70% (v/v) acetone. The dried crude extract was dissolved in ethanol and fractionated on a Sephadex LH-20 column using 95% (v/v) ethanol as the mobile phase. Five major fractions were isolated according to the UV absorption. All fractions exhibited marked antioxidant activity in a beta-carotene-linoleate model system. Fractions I and II showed the best preventive effect against the bleaching of beta-carotene. The scavenging effect of fractions I, III, and V, at 1 mg, on alpha, alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical was 67.4%, 80.7%, and 63.3%, respectively. Fractions II and IV showed weak DPPH scavenging effects. The reducing power of phenolics present in fractions IV and V was greater than that of fractions I-III, and the observed data correlated well (r(2) = 0.937; P = 0.007) with the total content of phenolics present in each fraction.