Antioxidant activity of alkylresorcinols from rye bran and their protective effects on cell viability of PC-12 AC cells.

Alkylresorcinols (ARs) are phenolic lipids that are present in high amounts in the bran layer of different cereals. Rye samples, cultivar Hazlet, and a white rye genotype, RT202, were analyzed for their antioxidant properties and AR content and composition, based on six fractions of the bran, where 1 was the outermost fraction and 6 was the bran fraction closest to the endosperm. Gas chromatography-mass spectrometry (GC-MS) analysis demonstrated that the most commonly found AR homologue in Hazlet rye is C19:0 and that the total amount of ARs decreases from the outermost to innermost fractions. The antioxidant activity using oxygen radical absorbance capacity (ORAC) for both white rye genotype RT202 and Hazlet brans was determined to decrease from the outermost fraction (136.05 µmol TE/g for Hazlet fraction 1 and 186.57 µmol TE/g for white rye genotype RT202 fraction 1) to the innermost fraction (9.84 µmol TE/g for Hazlet fraction 6 and 78.75 µmol TE/g for white rye genotype RT202 fraction 2). A positive relationship was seen with GC-MS results. Treatment of PC-12 AC cells with Hazlet fraction 1 increased mitochondrial biogenesis as determined using mitochondrial fluorescent dyes. In the presence of a prooxidant (AAPH), PC-12 AC cells were better protected from free radical attack when treated with Hazlet fraction 1 than with all other bran fractions. The results suggest that higher AR content in bran fractions confers antioxidant protection against free radical damage.

Evaluation of antioxidant capacity and aroma quality of breast milk.

OBJECTIVE: It is important to understand the difference and similarity in antioxidant capacity and aroma quality between formula and breast milk for purposes of modifying infant formulas. We evaluated the antioxidant properties and aroma quality of infant formula and breast milk. METHODS: Six breast milk samples and four infant formulas were used. Antioxidant properties were measured using the following methods: 2,2-diphenyl-1-picryhydrazyl free radical scavenging capacity, oxygen radical absorbance capacity, total phenolic content, and phenolic composition. Aroma quality was determined using the electronic nose. RESULTS: The 2,2-diphenyl-1-picryhydrazyl free radical scavenging activity for formula and breast milk ranged from 45.3% to 61.8% and from 52.8% to 61.2%, respectively. Oxygen radical absorbance capacity ranged from 28.8 to 31.9 g/kg for formula and from 25.5 to 39.2 g/kg for breast milk. Total phenolic content ranged from 422 to 751 mg/kg and from 329to 797 mg/kg for formula and milk, respectively. p-Hydroxybenzoic acid, p-coumaric acid, and ferulic acid were detected with values ranging from 614 to 635, 1391 to 1444, and 1425 to 1490 microg/kg in breast milk and from 783 to 3594, 1449 to 1510, and 1447 to 1561 microg/kg in formulas. Electronic nose results indicated that the aroma quality of formula controls 2, 3, and 4 was similar to that of breast milk. CONCLUSION: Differences and similarities in antioxidant properties and aroma quality were found among some of the formulas and breast milk. The contribution of phenolic acids to total antioxidant capacity was limited.

Patented techniques for the extraction and isolation of secoisolari-ciresinol diglucoside from flaxseed.

Plant lignans are phenolic compounds generally containing a dibenzylbutane skeleton. Secoisolariciresinol diglucoside (SDG) is the major lignan found in flaxseed. SDG is known to have antioxidant and anticancer properties. SDG can potentially be used as a natural antioxidant in foods thereby preventing further oxidation reactions and thus enhance the shelf life of foods. This article reviews the patents that are concerned with the extraction of SDG from flaxseed, the richest plant source of lignans. Most of the patented techniques for the extraction, isolation, and purification of SDG are conducted on defatted flaxseed and whole flaxseed. Flaxseed hull is potentially a good starting material. Furthermore, most methods use aliphatic alcohols (methanol, ethanol, isopropanol, butanol) to extract the complexed form of SDG. Combinations of these solvents are commonly used with water. Alkaline hydrolysis liberates SDG from its complexed form. SDG is enriched by a process involving either liquid-liquid partitioning or passing the aqueous phase through anion exchange resins or C18 resins. The SDG is recovered after evaporation of the water. Analytical HPLC coupled with mass spectrometry is performed to determine the quantity and purity of the extracted SDG.

Measurement of anthocyanins and other phytochemicals in purple wheat.

The major anthocyanin composition of normal purple wheat and heat stressed purple wheat were measured using HPLC, LC-MS/MS and the pH differential method. The lignan secoisolariciresinol diglucoside (SDG) and melatonin content were also measured. Total anthocyanin profile of normal purple wheat (491.3mg/kg) was significantly (P<0.05) lower than that of the heat stressed purple wheat (522.7mg/kg). Thirteen major anthocyanins were isolated and cyanidin 3-glucoside was the predominant anthocyanin in purple wheat. Using the pH differential method, the total anthocyanin content of normal (500.6mg/kg) and heat stressed (526.0mg/kg) purple wheat were similar to those observed using HPLC. The SDG content of normal and heat stressed purple wheat were 770 and 520µg/kg, while melatonin content was 4 and 2µg/kg, respectively. The presence of SDG and melatonin in addition to anthocyanins may contribute to the health benefits associated with consumption of coloured cereal grains.

Saskatoon and wild blueberries have higher anthocyanin contents than other Manitoba berries.

Studies have shown that anthocyanins present in berry fruits have some beneficial health effects such as reducing age-associated oxidative stress and possessing anti-inflammatory properties. Therefore, six Manitoba berries (wild blueberry, Saskatoon berry, raspberry, chokecherry, strawberry, and seabuckthorn) were studied for their anthocyanin compositions (mg/100 g) on dry weight basis. Saskatoon berry and wild blueberry showed a high content of total anthocyanins (562.4 and 558.3 mg/100 g, respectively) that were not significantly (P>0.05) different from each other. The corresponding values for other berries: raspberry (365.2 mg/100 g), chokecherry (177.39 mg/100 g), and strawberry (97.5 mg/100 g) were significantly different from each other (P<0.05), and the total anthocyanin content of seabuckthorn was negligible (0.84 mg/100 g). Fifteen major anthocyanins were isolated from Manitoba berries. Saskatoon berry and wild blueberry contained higher amounts of delphinidin 3-glucoside (Dp-3-glc), malvidin 3-glucoside (Mv-3-glc), and malvidin 3-galactoside (Mv-3-gal). Dp-3-glc was 263.8 (mg/100 g) in Saskatoon berry and 84.4 (mg/100 g) in wild blueberry, whereas the corresponding values for Mv-3-glc in these berries were 47.4 and 139.6 (mg/100 g), respectively. Raspberry, strawberry, and chokecherry contained higher amounts of cyanidin 3-glucoside (Cy-3-glc), cyanidin 3-rutinoside (Cy-3-rut), and pelargonidin 3-glucoside (Pg-3-glc). The total anthocyanin content of Manitoba fruits followed the order: Saskatoon berry and blueberry (high anthocyanin berries), raspberry and chokecherry (medium anthocyanin berries), strawberry (low anthocyanin berries), and seabuckthorn (negligible anthocyanin berries). This study demonstrated that Saskatoon berries and wild blueberries have high potential value for fruit growers as well as the food and nutraceutical manufacturers because of their high anthocyanin contents.

Proanthocyanidin profile and ORAC values of Manitoba berries, chokecherries, and seabuckthorn.

Six Manitoba fruits were analyzed for their phytochemical content and antioxidant activity in order to increase their production and marketability. The major proanthocyanidins (flavanols) present in whole fruit, juice, and pulp of strawberry, Saskatoon berry, raspberry, wild blueberry, chokecherry, and seabuckthorn were measured. The extraction and purification were facilitated using flash column chromatography, while separation and identification were accomplished by using HPLC and LC-MS techniques. The total proanthocyanidin contents varied from 275.55 to 504.77 mg/100 g in the whole fruit samples. Raspberry contained the highest content, and seabuckthorn showed the lowest content of total flavanols. The highest concentration of proanthocyanidin in juice was found in Saskatoon berry (1363.34 mg/100 mL) and the lowest value in strawberry (622.60 mg/100 mL). HPLC and LC-MS results indicated that epicatechin was the most abundant flavanol followed by B2 in the berry samples, while no catechin or B1 was detected in these fruits. A series of oligomers and polymers were detected in all samples. The recovery percentage was obtained from the ratio of the unspiked samples to the area of spiked samples. Monomers, dimers, oligomers, and polymers gave recovery ranges of 83-99%. The lipophilic and hydrophilic antioxidant capacities of whole fruit, juice, and pulp extracts were measured by the oxygen radical absorbance capacity (ORAC) procedure. In whole fruits, the ORAC values varied from 135 to 479 mg/100 g TE in the MeOH fraction. The corresponding ORAC values varied from 115.30 to 733.15 mg/100 g for the acetone fraction. In juice, all berries showed the same antioxidant capacity (P > 0.05) (133.0-312.0 mg/100 g) in the MeOH fraction, with the exception of raspberry (603.0 mg/100 g). Overall, MeOH fractions mainly contained monomers and dimers with smaller amounts of oligomers and polymers when compared to the acetone fractions. Acetone fractions mainly contained polymers and some oligomers. Although acetone fractions contained a higher quantity of total proanthocyanidins, their antioxidant capacities were lower than MeOH fractions.

AAPH-mediated antioxidant reactions of secoisolariciresinol and SDG.

Secoisolariciresinol (SECO ) is the major lignan found in flaxseed (Linum usitatissimum L.) and is present in a polymer that contains secoisolariciresinol diglucoside (SDG ). SECO, SDG and the polymer are known to have a number of health benefits, including reduction of serum cholesterol levels, delay in the onset of type II diabetes and decreased formation of breast, prostate and colon cancers. The health benefits of SECO and SDG may be partially attributed to their antioxidant properties. To better understand their antioxidant properties, SECO and SDG were oxidized using 2,2'-azobis(2-amidinopropane), an in vitro model of radical scavenging. The major lignan radical-scavenging oxidation products and their formation over time were determined. SDG was converted to four major products, which were the result of a phenoxyl radical intermediate. One of these products, a dimer of SDG, decomposed under the reaction conditions to form two of the other major products, and . SECO was converted to five major products, two of which were also the result of a phenoxyl radical intermediate. The remaining products were the result of an unexpected alkoxyl radical intermediate. The phenol oxidation products were stable under the reaction conditions, whereas two of the alcohol oxidation products decomposed. In general, only one phenol group on the lignans was oxidized, suggesting that the number of phenols per molecule may not predict radical scavenging antioxidant ability of lignans. Finally, SECO is a superior antioxidant to SDG, and it may be that the additional alcohol oxidation pathway contributes to its greater antioxidant ability.