Continuous abrasive method for mechanically fractionating flaxseed

Both the flaxseed hull, which is rich in the lignan secoisolariciresinol diglucoside (SDG), and the embryo, which is rich in oil with high α-linolenic acid content, are of interest for functional food use. A mechanical process for preparing hull-and embryo-rich fractions was developed and characterized. The process consisted of three pearlers, a sifter that yielded fines, and a gravity table that yielded final hull and embryo fractions. The SDG contents of fractions correlated inversely with oil content, showing that oil content indicated purity of both embryo and hull fractions and that the fines were essentially hull particles. Process performance depended on seed variety, moisture content, and feed rate; the best yields were 285 g hull +fines/kg for low-moisture Omega flaxseed, and 470 g embryo/kg seed for low-moisture Neche. Corresponding oil contents of those fractions were 28.8 and 47.4%, respectively. This process appears to be commercially feasible, provided it can be scaled up. A single stage was used to identify features that should be incorporated into a scaled-up unit, for example a 7-mesh screen in the pearler chamber rather than 6- or 8-mesh, and use of an overhead feed inlet to the chamber to direct seed into the disk-plate gap.     

Characterization of a Partially Purified Extract from Flax (Linumusitatissimum L.) Seed

A water‐soluble partially purified extract from defatted flax seed was obtained and characterized; it contained proteins (828.8 g/Kg), as well as water‐soluble carbohydrates (101.4 g/Kg) and phenolic compounds (22.2 g/Kg), essentially secoisolariciresinol diglucoside (SDG, 18.40 g/Kg) and ferulic acid (1.45 g/Kg) and p–coumaric acid (2.07 mg/kg) mainly in their glycoside forms. Proteins of 23–24 kDa were the main protein fractions found in the extract. In an emulsion model system, the flax extract was able to inhibit the production of oxidation products (conjugated diene, peroxides and aldehydes) as well as the degradation of flax oil carotenoids. The antioxidant effects of the flax extract were concentration dependent. Oxidation kinetics of the emulsion supplemented with 0.10 % flax extract were similar to the oxidation kinetics of the control blank, whereas, oxidation parameters of the emulsion supplemented with 0.48 % (and higher) flax extract were equal to or better than the oxidation parameters obtained with the test control emulsion containing 0.01 % BHT. These results suggested that flax seed phenolic compounds (SDG) and low molecular weight proteins, both found in the studied extract, might have very strong antioxidant properties. This is paper number 1089 of the Canadian Grain Commission.     

The Flaxseed-Derived Lignan Phenolic Secoisolariciresinol Diglucoside (SDG) Protects Non-Malignant Lung Cells from Radiation Damage

Plant phenolic compounds are common dietary antioxidants that possess antioxidant and anti-inflammatory properties. Flaxseed (FS) has been reported to be radioprotective in murine models of oxidative lung damage. Flaxseed’s protective properties are attributed to its main biphenolic lignan, secoisolariciresinol diglucoside (SDG). SDG is a free radical scavenger, shown in cell free systems to protect DNA from radiation-induced damage. The objective of this study was to investigate the in vitro radioprotective efficacy of SDG in murine lung cells. Protection against irradiation (IR)-induced DNA double and single strand breaks was assessed by γ-H2AX labeling and alkaline comet assay, respectively. The role of SDG in modulating the levels of cytoprotective enzymes was evaluated by qPCR and confirmed by Western blotting. Additionally, effects of SDG on clonogenic survival of irradiated cells were evaluated. SDG protected cells from IR-induced death and ameliorated DNA damage by reducing mean comet tail length and percentage of γ-H2AX positive cells. Importantly, SDG significantly increased gene and protein levels of antioxidant HO-1, GSTM1 and NQO1. Our results identify the potent radioprotective properties of the synthetic biphenolic SDG, preventing DNA damage and enhancing the antioxidant capacity of normal lung cells; thus, rendering SDG a potential radioprotector against radiation exposure.     

Modeling the recovery patterns from solid phase extraction purification of secoisolariciresinol diglucoside,p-coumaric acid glucoside,and ferulic acid glucoside from microwave-assisted flaxseed extracts

Flaxseed extracts obtained by microwave-assisted extraction (MAE) were cleaned of leftover salts from hydrolysis by solid phase extraction (SPE). The SPE set up was affordable, non-automated and vacuum-driven. The recovery patterns of secoisolariciresinol diglucoside (SDG), p-coumaric acid glucoside (PCouAG), and ferulic acid glucoside (FerAG) were modeled in two stages using regression procedures (p < 0.05). At stage one, the recovery patterns were predicted as a function of SPE eluent concentration in ethanol (10–50%). At stage two, the accuracy of the predictions was increased by enlarging the SPE eluent regressor's range (0–100% ethanol in water) and arranging the solvent system into three practical elution groups. The groups 1, 2 and 3 reflected the major loss, the major recovery and the minor loss of SDG, respectively. Second degree polynomial regression models were fitted for accurately predicting the recoveries of compounds. Microwave-assisted extracts obtained from 0.6 and 1.5 g defatted flaxseed meal were purified; the total SDG recoveries from the SPE funnel were 97.8 and 99.8%; and the SDG amounts obtained were 8.54 and 20 mg, respectively. The HPLC analysis of eluates pooled into practical groups allows for significant reductions in HPLC analysis time and solvent consumption which could have a positive impact on future purification studies. The results of this study allow for designing simplified, efficient and economical pilot scale studies for the purification of SDG from flaxseed extracts.     

Antioxidant Activity of Piceatannol in Canola Oil

Piceatannol has shown to be a strong antioxidant in vivo, however, its ability to suppress lipid oxidation in foods has not been examined. The present study is to examine the antioxidant effect of piceatannol on heated canola oil compared with that of butylated hydroxytoluene (BHT). The oxidation of canola oil is conducted at 60, 90, 120, and 150 °C by monitoring the depletion of oxygen, the decrease in unsaturated fatty acids, and the changes of primary and secondary oxidation products. Results demonstrated that piceatannol can suppress lipid oxidation of canola oil in a dose-dependent manner with its effect being more effective than BHT. Practical Applications: Lipid oxidation is a major factor in the deterioration of food quality. Synthetic antioxidants, such as BHT and butylated hydroxyanisole, are used to inhibit oxidation in foods, but their safety has been always concerned. Piceatannol has exhibited a strong antioxidant activity to attenuate lipid oxidation and it should be further explored for use as a natural antioxidant in foods.     

Extraction and identification of natural antioxidant from the seeds of the Moringa oleifera tree variety of Malawi

The oil from the dried seeds of the Moringa oleifera tree (variety of Malawi) was extracted with a mixture of chloroform/methanol (50∶50). The induction period measurements demonstrated a great resistance to oxidative rancidity. After degumming, there was a reduction of 74% in induction periods. The gums produced were extracted with diethylether, n-butanol, and water, yielding four fractions: Fraction 1 (81.8% w/w), Fraction 2 (0.04% w/w), Fraction 3 (0.05% w/w), and Fraction 4 (17.0% w/w). These fractions were tested for their protection of fresh sunflower oil against rancidity, at 50°C, using a UV accelerated method. The oxidation of the sunflower oil was measured using PV; absorbance E _1cm ^1% and malondialdehyde concentration were measured by HPLC. The fraction that showed the highest antioxidant activity was further fractionated by HPLC, yielding seven fractions. Fraction HPLC 3 (present in a quantity of 330.8 and 29.11 ppm in gums and oil, respectively) showed the highest antioxidant activity. Its activity was also compared with that of the commonly used antioxidants BHT and α-tocopherol on sunflower oil using the same methods. At the same level of addition (200 ppm), HPLC 3 showed higher antioxidant activity than BHT and α-tocopherol. The identification of HPLC3 was done using ¹H NMR, ¹³C NMR, MS, melting point, and UV absorption spectroscopy and proved to be 3,5,7,3′,4′,5′-hexahydroxyflavone (myricetin).     

Genotype and growing location effects on phytosterols in canola oil

There is little information available about phytosterols in canola (Brassica napa L.) oil and the effects of genotype and growing locations from Virginia and the mid-Atlantic region of the United States, a potential area for the establishment of domestic production to provide edible oil. Our objectives were to characterize the phytosterols, phospholipids, unsaponifiable matter, and FA in oil from Virginia-grown canola. Among 11 canola genotypes grown at two locations during 1995–1996 significant variations existed for oil content and FA profiles, but not for contents of phospholipids, unsaponifiable matter, total phytosterols, campesterol, stigmasterol, and β-sitosterol, Total phytosterol content in the oil of Virginia-grown canola varied from 0.7 to 0.9% with a mean of 0.8%. This concentration compared favorably with oil from Canadian canola, which typically contains 0.5 to 1.1% total phytosterols. The mean contents of brassicasterol, campesterol, stigmasterol, β-sitosterol, Δ⁵-avenasterol, and Δ⁷-stigmatenol as percentages of total phytosterols in Virginia-grown canola were: 9.7, 32.0, 0.6, 49.3, 4.99, and 3.5%, respectively. Growing location did not affect phytosterols in Virginia-grown canola oil but had significant effects on contents of phospholipids, and saturated (myristic, stearic, and arachidic) and unsaturated (palmitoleic, linoleic, linolenic, eicosenoic, and erucic) FA.     

Effect of Extraction Method on the Phenolic and Cyanogenic Glucoside Profile of Flaxseed Extracts and their Antioxidant Capacity

The application of flaxseed extracts as food ingredients is a subject of interest to food technologists and nutritionists. Therefore, the influence of the extraction method on the content and composition of beneficial compounds as well as anti‐nutrients is important. In the study, the effects of two solvent extraction methods, aqueous and 60 % ethanolic, on phenolic and cyanogenic glucoside profiles of flaxseed extract were determined and compared. The impact of extracted phenolic compounds on the antioxidant capacity of the extracts was also investigated. Defatted meals from brown and golden flax varieties were used as extraction material. The ethanolic extraction was more selective for phenolics (100.8–131.7 mg g^?1) than the aqueous one (11.5–15.7 mg g^?1). However, the contribution of particular phenolic compounds to total phenolics was much more dependent on flax variety than extraction method. A strong relationship was observed between both radical scavenging and ferric reducing activity and the content of phenolics (particularly secoisolariciresinol diglucoside). The correlation between extract chelating ability and phenolics was moderate suggesting that other flaxseed compounds are involved in this activity. The extraction method strongly affected cyanogenic glucoside content of flaxseed extracts; the aqueous extraction caused 96 % reduction in cyanogenic glucoside content (0.56–0.62 mmol g^?1) when compared to the content in defatted meal (9.1–11.6 mmol g^?1). On the contrary, ethanolic extraction resulted in the high cyanogenic glucoside content in the extracts (71–89 mmol g^?1). The results reveals that ethanolic extraction gives extracts rich in antioxidant lignans; aqueous extracts have lower antioxidant activity than ethanolic but cyanogenic glucosides are significantly reduced.     

Changes in the Content of Phenolic Compounds in Flaxseed Oil During Development

The phenolic fraction of flaxseed oil was quantified during the development of three varieties (H52, O116 and P129). Seed samples were collected at regular intervals from 7 to 56 days after flowering (DAF). During oilseed processing, less polar compounds are co-extracted with oil. The methanolic extracts were obtained by solid phase extraction. Separation of phenolic compounds was conducted by high-performance liquid chromatography-mass spectrometry. The main phenolic compounds detected during maturation were: diphyllin, pinoresinol, matairesinol, secoisolariciresinol, vanillic acid, ferulic acid and vanillin. The highest amount of lignans (6.74 mg of analyte/kg of flaxseed oil) was detected at 7 DAF in P129 variety. The maximum level of phenolic acids (2.57 mg of analyte/kg of flaxseed oil) was reached at 7 DAF in P129 which had also the highest content of simple phenols (1.37 mg of analyte/kg of flaxseed oil) at the same date after flowering. At full maturity, the content of phenolic compounds in three varieties ranged from 0.26 to 0.36 mg of analyte/kg of flaxseed oil. The highest content of total phenolic compounds using the Folin–Ciocalteu method was detected in P129 variety (196.42 mg CAEs/kg of flaxseed oil) at 7 DAF. Results of this study indicate that flaxseed oils contain different amounts of phenolic compounds using different methods.     

Low erucic acid canola oil does not induce heart triglyceride accumulation in neonatal pigs fed formula

Canola oil is not approved for use in infant formula largely because of concerns over possible accumulation of triglyceride in heart as a result of the small amounts of erucic acid (22∶1n−9) in the oil. Therefore, the concentration and composition of heart triglyceride were determined in piglets fed from birth for 10 (n=4–6) or 18 (n=6) d with formula containing about 50% energy fat as 100% canola oil (0.5% 22∶1n−9) or 100% soybean oil, or 26% canola oil or soy oil (blend) with palm, high-oleic sunflower and coconut oil, providing amounts of 16∶0 and 18∶1 closer to milk, or a mix of soy, high-oleic sunflower and flaxseed oils with C₁₆ and C₁₈ fatty acids similar to canola oil but without 22∶1. Biochemical analysis found no differences in heart triglyceride concentrations among the groups at 10 or 18 d. Assessment of heart triglycerides using Oil Red O staining in select treatments confirmed no differences between 10-d-old piglets fed formula with 100% canola oil (n=4), 100% soy oil (n=4), or the soy oil blend (n=2). Levels of 22∶1n−9 in heart triglyceride and phospholipid, however, were higher (P<0.01) in piglets fed 100% canola oil or the canola oil blend, with higher levels found in triglycerides compared with phospholipids. The modest accumulation of 22∶1n−9 associated with feeding canola oil was not associated with biochemical evidence of heart triglyceride accumulation at 10 and 18 d.     

Identification,in vitro and in vivo Antioxidant Activity,and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract

Lignans are generally known for their beneficial impact on human health. In this study, we found that the water extract of silver fir (Abies alba) wood contains lignans, which constitute approximately 10% of the extract and include isolariciresinol, hydroxymatairesinol, secoisolariciresinol, lariciresinol, pinoresinol, and matairesinol. The antioxidant activity of the extract was measured by several in vitro assays and an assay in a eukaryotic cell model (yeast). The extract had greater in vitro antioxidative activity than ascorbic acid, resveratrol, or butylated hydroxytoluene (BHT) and similar antioxidative activity to epigallocatechin gallate. The intracellular antioxidant effect in the yeast gave indirect evidence that the components of the silver fir wood extract (SFWE) effectively pass through eukaryotic cell membranes and have higher in vivo antioxidative activity than ascorbic acid, resveratrol, tocopheryl succinate, or BHT and similar to epigallocatechin gallate. The in vitro gastrointestinal digestion of the lignans in the extract is not significant; therefore, it is reasonable to expect antioxidative effects from orally applied SFWE.     

Antioxidant activity of flavonoids isolated from Scutellaria rehderiana

The present study examined the antioxidant activity in heated canola oil of hexane, acetone, and methanol extracts of dry roots of gansu huangqin (Scutellaria rehderiana) as well as six flavonoids isolated from the acetone and methanol extracts. The oxidation was conducted at 95°C by monitoring oxygen consumption and decreases in both linoleic and α-linolenic acids. The acetone extract was most effective in inhibiting oxidation of canola oil, followed by the methanol extract. The antioxidant activity of gansu huangqin acetone extract was dose-dependent. Among the six flavonoids, baicalein and ganhuangenin were more effective than butylated hydroxytoluene (BHT) in protecting canola oil from oxidation. The present results suggest that the acetone extract of this root may be a potential source of natural antioxidants for use in processed foods.     

Antioxidant activity of tea theaflavins and methylated catechins in canola oil

The present study examined the antioxidant activity of black tea theaflavins and catechin derivatives in canola oil. Oxidation was conducted at 95°C by monitoring the oxygen consumption and decreases in the linoleic and α-linolenic acids of canola oil. All were tested at a concentration of 0.5 mM. Catechins, including (−)-epicatechin, (−)-epicatechin gallate, (−)-epigallocatechin, and (−)-epigallocatechin gallate (EGCG), were more effective than theaflavins, namely, theaflavin-1, theaflavin-3-gallate, theaflavin-3′-gallate, and theaflavin-3,3′-digallate (TF₃), against the lipid oxidation of canola oil. Among the four theaflavins, TF₃ was the most effective, whereas among the four catechins, FGCG was the most potent. Under the same conditions, all theaflavins and catechins were more powerful than BHT as an antioxidant in heated canola.oil. Little or no difference in antioxidant activity was observed between each catechin and epimer pair. Methylation of the 3′-OH led to a significant loss of antioxidant activity of the catechins.     

Antioxidant Activity of Sesamin in Canola Oil

The present study presents the antioxidant activity of sesamin in canola oil compared with that of butylated hydroxytoluene (BHT) by monitoring the oxygen consumption and the decrease in linoleic acid and α-linolenic acid. The oxidation of canola oil was conducted at 35, 60, 90, 120 and 180 °C with addition of 50–400 ppm sesamin. Results from the oxygen consumption test showed that sesamin dose-dependently inhibited the oxidation of canola oil at concentrations of 50–200 ppm at temperatures of 60–180 °C, however, sesamin lost its antioxidant activity at a low temperature of 35 °C. The fatty acid analysis also demonstrated that sesamin at 50, 100 and 200 ppm dose-dependently prevented the oxidation of linoleic acid and α-linolenic acid in canola oil. Both the oxygen consumption and the fatty acid analysis demonstrated sesamin was less effective than BHT as an antioxidant at temperatures of 60–180 °C. It was therefore concluded that sesamin could prevent the lipid oxidation of frying fats and oil, however, its antioxidant activity was not as potent as that of BHT.     

Effects of β-carotene and lycopene thermal degradation products on the oxidative stability of soybean oil

The relative oxidative stability of soybean oil samples containing either thermally degraded β-carotene or lycopene was determined by measuring peroxide value (PV) and headspace oxygen depletion (HOD) every 4 h for 24 h. Sobyean oil samples containing 50 ppm degraded β-carotene that were stored in the dark at 60°C displayed significantly (P<0.01) higher HOD values compared with controls. Lycopene degradation products (50 ppm) in soybean oil significantly (P<0.05) decreased HOD of samples when stored in the dark. PV and HOD values for samples containing 50 ppm of either β-carotene or lycopene degradation products stored under lighted conditions did not differ significantly from controls (P<0.05). However, soybean oil samples containing 50 ppm of unheated, all-trans β-carotene or lycopene stored under light showed significantly lower PV and HOD values than controls (P<0.01). These results indicated that during autoxidation of soybean oil held in the dark, β-carotene thermal degradation products acted as a prooxidant, while thermally degraded lycopene displayed antioxidant activity in similar soybean oil systems. In addition, β-carotene and lycopene degradation products exposed to singlet oxygen oxidation under light did not increase or decrease the oxidative stability of their respective soybean oil samples.     

Inhibition of malonaldehyde formation by antioxidants from ω3 polyunsaturated fatty acids

The inhibitory effect of α-tocopherol, β-carotene, 2″-O-glycosyl isovitexin (2″-O-GIV), and butylated hydroxytoluene (BHT) on malonaldehyde (MA) formation from ω3 polyunsaturated fatty acids (PUFA) was determined by gas chromatography. The levels of MA formed from 1 mg each of octadecatetraenoic acid (ODTA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) upon oxidation with Fenton's reagent were 29.8±1.5, 17.2±1.5, and 22.0±0.7 nmol, respectively. BHT was most effective toward protecting all three ω3 PUFA, whereas β-carotene did not exhibit any inhibitory effect. 2″-O-GIV inhibited MA formation from EPA and DHA by 56 and 43%, respectively, showing the second greatest inhibitory activity after BHT. α-Tocopherol inhibited MA formation from ODTA and DHA by 67 and 28%, respectively, but it did not show any activity toward EPA oxidation. The naturally occurring antioxidant, 2″-O-GIV, may be useful to prevent oxidation of ω3 PUFA.     

Optimal tocopherol concentrations to inhibit soybean oil oxidation

The optimal concentration for tocopherols to inhibit soybean oil oxidation was determined for individual tocopherols (α-, γ-, and δ-tocopherol) and for the natural soybean oil tocopherol mixture (tocopherol ratio of 1∶13∶5 for α-, γ-, and δ-tocopherol, respectively). The concentration of the individual tocopherols influenced oil oxidation rates, and the optimal concentrations were unique for each tocopherol. For example, the optimal concentrations for α-tocopherol and γ-tocopherol were ∼100 and ∼300 ppm, respectively, whereas δ-tocopherol did not exhibit a distinct concentration optimum at the levels studied (P<0.05). The optimal concentration for the natural tocopherol mixture ranged between 340 and 660 ppm tocopherols (P<0.05). The antioxidant activity of the tocopherols diminished when the tocopherol levels exceeded their optimal concentrations. Above their optimal concentrations, the individual tocopherols and the tocopherol mixture exhibited prooxidation behavior that was more pronounced with increasing temperature from 40 to 60°C (P<0.05). A comparison of the antioxidant activity of the individual tocopherols at their optimal concentrations revealed that α-tocopherol (∼100 ppm) was 3–5 times more potent than γ-tocopherol (∼300 ppm) and 16–32 times more potent than δ-tocopherol (∼1900 ppm).     

Pheophytin α degradation products as useful indices in the quality control of virgin olive oil

In previous studies we reported the presence of compounds with spectral characteristics similar to pheophytin α (Pheo α), which often accompany the Pheo α peak in the chromatographic profile of virgin olive oils (VOO) at 410 nm under normal-phase HPLC conditions. The occurrence and levels of these compounds were found to be affected by storage conditions of the oil samples. In the present study we investigated whether the major Pheo a degradation products, identified as pyropheophytin α (coeluting with the respective epimer) and 13²-OH-pheophytin α, could be used as estimates of VOO history. The content of Pheo α and its degradation products was determined for a great number of authentic olive oil samples of unknown history. Results are discussed in comparison with other quality indices (e.g., antioxidant content) when necessary. High amounts of the pyro form (20–30% of total pheophytins) were related to thermal abuse or lengthy storage. The presence of allomers indicated oxygen availability. The levels of these products, 0–20% of the total pheophytin content for 62% of the samples, seemed to be influenced by the presence of pro- and antioxidants. When low levels of Pheo α are not accompanied by other degradation products, light exposure for a certain period of storage can be assumed.     

The influence of carotenoids and tocopherols on the stability of safflower seed oil during heat-catalyzed oxidation

The stability and antioxidant effects of carotenoids and tocopherols in safflower seed oil were evaluated under thermal (75°C) and oxidative conditions and the oxidative stability index (OSI) determined. The antioxidant capability of butylated hydroxytoluene (BHT) was also compared with that of β-carotene in a model system. Lycopene and β-carotene (1 to 2000 ppm) were heated (75°C) and exposed to air (2.5 psi) in an oxidative stability instrument. β-Carotene had no antioxidant effect at concentrations below 500 ppm, because it did not alter the induction time. Lycopene increased the induction time only slightly at low concentrations. However, at concentrations greater than 500 ppm, both β-carotene and lycopene acted as prooxidants, significantly decreasing the induction period. At the highest concentration, 2000 ppm, lycopene was more prooxidative than β-carotene. α- and γ-Tocopherol (concentration, 1000 ppm) delayed the induction time by 16 and 26 h, respectively. There was no cooperative interaction between α-tocopherol and β-carotene in delaying the onset of oxidation. Furthermore, BHT was significantly more antioxidative than β-carotene. Thus, under thermal and oxidative conditions, β-carotene could not delay the onset of oxidation. The tocopherols and BHT were effective in suppressing the onset of oxidation, as determined by the oxidative stability measurement.     

Canola extract as an alternative natural antioxidant for canola oil

The antioxidative activity of ethanolic extracts of canola meal at 100, 200, 500 and 1000 ppm on refined-bleached (RB) canola oil was examined and compared with commonly used synthetic antioxidants, such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), BHA/BHT/monoglyceride citrate (MGC) andtert-butyl-hydroquinone (TBHQ). Stability of RB oil was monitored under Schaal oven test conditions at 65°C over a 17-d period. Progression of oxidation was monitored by weight gain, peroxide, conjugated diene, 2-thiobarbituric acid and total oxidation values. Canola extracts at 500 and 1000 ppm were more active than BHA, BHT and BHA/BHT/MGC and less effective than TBHQ at a level of 200 ppm.