Antioxidant polyphenols from tart cherries (Prunus cerasus).

Montmorency and Balaton tart cherries were lyophilized and sequentially extracted with hexane, ethyl acetate, and methanol. Methanolic extracts of dried Balaton and Montmorency tart cherries (Prunus cerasus) inhibited lipid peroxidation induced by Fe(2+) at 25 ppm concentrations. Further partitioning of this methanol extract with EtOAc yielded a fraction that inhibited lipid peroxidation by 76% at 25 ppm. Purification of this EtOAc fraction afforded eight polyphenolic compounds, 5,7,4'-trihydroxyflavanone (1), 5,7, 4'-trihydroxyisoflavone (2), chlorogenic acid (3), 5,7,3', 4'-tetrahydroxyflavonol-3-rhamnoside (4), 5,7,4'-trihydroxyflavonol 3-rutinoside (5), 5,7,4'-trihydroxy-3'methoxyflavonol-3-rutinoside (6), 5,7,4'-trihydroxyisoflavone-7-glucoside (7), and 6, 7-dimethoxy-5,8,4'-trihydroxyflavone (8), as characterized by (1)H and (13)C NMR experiments. The antioxidant assays revealed that 7-dimethoxy-5,8,4'-trihydroxyflavone (8) is the most active, followed by quercetin 3-rhamnoside, genistein, chlorogenic acid, naringenin, and genistin, at 10 microM concentrations.

Novel antioxidant compounds from tart cherries (Prunus cerasus).

As indicated by an Fe(II)-induced liposome peroxidation bioassay, the EtOAc extract of tart cherries (Prunus cerasus) was found to have strong antioxidant activity. Purification of this extract afforded chlorogenic acid methyl ester (1) and three novel compounds, 2-hydroxy-3-(o-hydroxyphenyl) propanoic acid (2); 1-(3', 4'-dihydroxycinnamoyl)-cyclopenta-2,5-diol (3), and 1-(3', 4'-dihydroxycinnamoyl)-cyclopenta-2,3-diol (4), as determined by their spectral data. At a 20-microM concentration, the antioxidant activities of compounds 3 and 4 were comparable to the antioxidant activities of caffeic acid, whereas compound 1 showed activity similar to chlorogenic acid. Also, these compounds showed antioxidant activities similar to the commercial antioxidants tert-butylhydroquinone and butylated hydroxytoluene. However, compound 2 was not active when tested at a 100-microM concentration.

Effect of dietary administration of oil extracts from rosemary and sage on lipid oxidation in broiler meat.

1. Oxidation of meat and membrane from broilers fed on a diet containing 500 mg/kg rosemary and sage extracts was compared to meat and membrane oxidation from broilers receiving a control diet (not enriched with antioxidants) and a diet enriched in alpha-tocopheryl acetate (200 mg/kg). 2. After 9 d of refrigerated storage, thiobarbituric acid reactive substances of white meat from broilers fed on the control and the alpha-tocopheryl acetate-enriched diets were 0.51 and 0.25 mg malonaldehyde/kg meat, respectively. Values for meat from broilers fed on the diets containing the rosemary and sage extracts were in the range 0.30 to 0.35 mg malonaldehyde/kg meat, significantly lower than those from birds fed on the control diet. A similar trend was observed in the dark meat but differences were not significant at 9 d of storage. Similar trends were observed in raw samples stored at -20 degrees C for up to 4 months and in samples cooked at 70 degrees C and kept stored under refrigeration for up to 4 d. 3. The meat from broilers fed on the diet containing spice extracts had smaller concentrations of total cholesterol oxidation products (COPS) than meat from the control group (P < 0.05). Supplemental alpha-tocopheryl acetate reduced the COPS concentrations to a greater extent than did spice extracts (P < 0.05). 4. A similar trend was observed in microsomal fraction isolates, in which the rate of metmyoglobin/hydrogen peroxide-catalysed lipid peroxidation was lower in animals receiving spice extracts than in those fed on the basal diet.

Effect of dietary oat administration on lipid stability in broiler meat.

1. The susceptibility to oxidation of meat from broilers receiving 200 g/kg oats in the diet was compared to the stability of meat from broilers receiving a control diet (10 mg/kg of alpha-tocopheryl acetate) and a diet enriched in alpha-tocopheryl acetate (200 mg/kg). 2. After 9 d of refrigerated storage thiobarbituric acid-reactive substances (TBARS) values in raw dark meat (thigh) were 0.51 and 0.19, respectively, for broilers fed on the control and the alpha-tocopheryl acetate-enriched diets. Meat from broilers fed on the diet containing oats had a lower TBARS value than the control group (P < 0.05), but higher than the group receiving the supplemented diet. The same trend was observed in white meat (breast). Similar effects were observed after the frozen storage of meats, although the antioxidant effect of oats was more evident (P < 0.05) than in the raw meat. 3. Cholesterol oxidation products (COPS) in broiler meat were also influenced by the dietary regimen. COPS concentration in white and dark meat, respectively, from broilers fed on the oat diet were 43% and 32% lower than those in the control samples. 4. Supplemental alpha-tocopheryl acetate reduced COPS concentration by approximately 60%. The availability of natural antioxidants and their possible synergistic effects suggest an interesting way of improving meat stability.

Dietary vegetable oils and alpha-tocopherol reduce lipid oxidation in rabbit muscle.

This experiment was conducted to study the effect of dietary vegetable oil on lipid oxidation in rabbit muscle. A control diet with no added fat and two diets with olive or sunflower oil (30 g/kg) were used. Within each treatment, one group was fed a low level of alpha-tocopheryl acetate (10 mg/kg diet), and the other a supplemental level (200 mg/kg). Rabbits were fed experimental diets from weaning (20 d) to slaughter (69 d). The supplemental level of dietary alpha-tocopheryl acetate produced higher alpha-tocopherol concentration in muscle (P < 0.006) and lower lipid oxidation (P < 0.004). Rabbits that received sunflower oil had higher concentrations of thiobarbituric acid reactive substances than rabbits that consumed olive oil (P < 0.05). Moreover, a significant effect due to fat inclusion in the diet was found. Muscles from rabbits fed diets not enriched with fat had higher susceptibility to lipid oxidation (P < 0.005) and higher concentration of (n-3) fatty acids in polar lipids (P < 0.04) than those from rabbits fed fat-enriched diets. A second experiment was conducted and confirmed the higher lipid oxidation in the muscle of rabbits fed diets not enriched with fat than in that of rabbits fed diets containing sunflower oil (28 g/kg) (P < 0.003) as well as in diets with identical digestible energy. In this experiment, alpha-tocopheryl acetate was at the lower level (10 mg/kg feed). Inclusion of oils rich in oleic (olive oil) or linoleic acid (sunflower oil) in rabbit diets reduces lipid oxidation in muscles.

Oxidative quality and shelf life of meats.

Lipid oxidation is one of the primary mechanisms of quality deterioration in foods and especially in meat products. The changes in quality are manifested by adverse changes in flavor, color, texture and nutritive value, and the possible production of toxic compounds. Lipid oxidation in muscle systems is initiated at the membrane level in the intracellular phospholipid fractions. How this occurs has still not been resolved, although it is generally believed that the presence of transition metals, notably iron, is pivotal in facilitating the generation of species capable of abstracting a proton from an unsaturated fatty acid. This paper provides an overview of how lipid oxidation affects the quality and shelf life of meat and meat products, and how shelf life can be extended through dietary vitamin E supplementation above requirement levels. The formation of cholesterol oxidation products and the possible role of lipids and their oxidation products in the formation of heterocyclic aromatic amines are also discussed.

Influence of dietary vitamin E on the oxidative stability and quality of pig meat.

Oxidation of lipids is a major cause of deterioration in the quality of muscle foods and can directly affect many quality characteristics such as flavor, color, texture, nutritive value, and safety of the food. Lipid oxidation in muscle systems is initiated at the membrane level in the intracellular phospholipid fractions. In the processing of muscle foods, one of the most important questions concerns the methods used to delay the initiation of oxidation and loss of quality. Vitamin E is a major lipid-soluble antioxidant, and one of its primary functions is to maintain and protect biological membranes against lipid peroxidation. Dietary vitamin E supplementation above requirement levels is effective in reducing lipid oxidation. This review focuses on the antioxidant function of vitamin E and how supplementation of the diet of pigs with vitamin E influences the rate of lipid peroxidation, color, water-holding capacity, and cholesterol oxidation in pig meat.

Further studies on n-nitrosopyrrolidine and its precursors: Effects of ascorbic acid and vitamin E on tumor development in mice as related to consumption of cured meat.

Two experiments were carried out to ascertain if supplementation of a semipurified diet to Swiss-ICR mice with either ascorbic acid (AA), vitamin E (Vit E) or a combination of the two would modulate the carcinogenic effects of N-nitrosopyrrolidine (NPyr) and of its probable precursors (nitrite-N0(2) and pyrrolidine-Pyr) in Experiment I or of NPyr in Experiment II. Results indicated that neither AA nor Vit E modulated the carcinogenic effects of NPyr or of its probable precursors (NO(2) and Pyr). Results verified a previous report from our laboratory showing that NPyr increased the number of malignant tumors by some 5-8 fold over controls. There was a lower incidence of tumors in the control group on the semi-purfied diet than in the groups given NO(2) and Pyr, although both treatments had a low frequency of malignant tumors (1 63 versus 5 72 survivors). Results support our earlier study suggesting that neither NO(2) nor Pyr alone or in combination together contribute to cancer-at least in the laboratory mouse.

Lipid peroxidation products are elevated in fish oil diets even in the presence of added antioxidants.

Purified corn and fish oil diets with different types and concentrations of antioxidants were evaluated for oxidation products. In addition, a determination of different organ and carcass oxidation product levels was performed. Peroxide value and thiobarbituric acid assays were performed on the diets immediately after mixing (0 h) and 24, 48 and 72 h after being fed to mice. The AIN-recommended level of antioxidant addition (butylated hydroxytoluene, 0.02 g/100 g oil) and even the addition of 100 times this level (2 g/100 g oil), although decreasing the level of oxidation products, failed to totally prevent oxidative deterioration in diets high in fish oil. Furthermore, other antioxidants added in excess to the fish oil diets also failed to completely suppress oxidative deterioration of the diets and, in addition, when fed daily to mice for a period of 4 wk, caused an accumulation of lipid peroxidation products in certain organs (e.g., heart, skeletal muscle, mammary glands) and in the carcass. These results provide evidence that in the preparation of fish oil diets, the addition of antioxidants at the AIN-recommended level, or even levels substantially higher, does not completely suppress oxidative deterioration of experimental diets.

Influence of dietary fat and α-tocopherol supplementation on lipid oxidation in pork.

Sixty-four pigs, approximately 3 weeks old, were fed diets containing 3% beef tallow or 3% soya oil with either a basal (10-50 mg/kg diet) or supplemented (200 mg/kg diet) level of α-tocopheral acetate. In pigs fed the soya oil diet the neutral and polar lipid fractions of muscle tissue and the total lipid fraction of adipose tissue had significantly (P < 0·05) higher C18:2/C18:1 ratios when compared to pigs fed the tallow diet. Muscle from pigs fed the soya oil diet was significantly more susceptible (P < 0·05) to lipid oxidation than muscle from pigs fed the tallow diet. In pigs receiving the α-tocopherol supplemented diet, α-tocopherol levels were approximately 3·3, 2·8 and 2-times higher in plasma, muscle and adipose tissue, respectively, when compared to pigs fed the basal level of α-tocopherol acetate. α-Tocopherol supplementation significantly increased (P < 0·05) the oxidative stability of muscle from pigs fed both the tallow and soya oil diets.

Effect of dietary fat on growth of MCF-7 and MDA-MB231 human breast carcinomas in athymic nude mice: relationship between carcinoma growth and lipid peroxidation product levels.

Human breast carcinoma cell lines MCF-7 and MDA-MB231 were transplanted s.c. to female athymic nude mice at 3-4 weeks of age. At 7-10 days after transplantation, the mice were divided into groups and fed for 6-8 weeks one of the following semi-purified diets containing different amounts and types of fat, i.e. 5% corn oil, 20% corn oil, 20% butter, 19% beef tallow/1% corn oil and 19% fish (Menhaden) oil/1% corn oil. In addition experiments, the fish oil diets were supplemented with antioxidants (vitamin E, 8 g or 2000 IU/kg diet plus tertiary butyl hydroquinone, TBHQ, 4 g/kg diet) or ferric citrate (3 g/kg diet). Tumor peroxidation product levels were assessed by measuring 2-thiobarbituric acid reactants (TBA assay). At the termination of the studies (6-8 weeks of diet feeding) mean human breast carcinoma volume (MCF-7 and MDA-MB231) was the largest in mice fed the 20% corn oil diet, intermediate in mice fed the butter or beef tallow diets and the least in mice fed the fish oil diet. The difference in mean tumor volumes among mice fed the 20% corn oil diet and those fed the fish oil diet was significant (P less than 0.01). When comparing low (5% corn oil) and high (20% corn oil) fat diets, numerical increases in human breast carcinoma volume (MCF-7 and MDA-MB231) were consistently observed in the high-fat diet groups but these differences were not always significant. Tumor lipid peroxidation product levels were determined on the MDA-MB231 tumors; tumor lipid peroxidation levels were significantly (P less than 0.01) increased only in mice fed the fish oil diets. Supplementation of the fish oil diets with antioxidants (vitamin E + TBHQ) significantly reduced the level of tumor peroxidation products and significantly increased tumor volume (P less than 0.05). When tumor lipid peroxidation product levels in the fish oil plus antioxidant fed mice were reduced to the level of that observed in the tumors of the corn oil fed mice, no significant differences in tumor volumes were observed in these two groups. In contrast, supplementation of the fish oil diets with ferric citrate, significantly (P less than 0.05) increased tumor lipid peroxidation product levels and decreased tumor volume. Thus, the type of dietary fat can clearly affect the growth of human breast carcinomas (MCF-7 and MDA-MB231) maintained in athymic nude mice.(ABSTRACT TRUNCATED AT 400 WORDS)

Effect of dietary Vitamin E on the stability of raw and cooked pork.

Experiments were designed to investigate the effects of dietary α-tocopherol supplementation for 2 weeks prior to slaughter on plasma and muscle α-tocopherol levels and on the oxidative stability of raw and cooked pig muscle during refrigerated storage at 4°C. Plasma and muscle α-tocopherol levels of the pigs on the α-tocopherol supplemented diet (200 mg α-tocopherol acetate/kg feed) were ∼2·5-fold higher than those of the pigs on the control diet (30 mg α-tocopherol acetate/kg feed). Dietary supplementation with α-tocopherol significantly (p < 0·01) improved the oxidative stability of both raw and cooked muscle after storage at 4°C for up to 8 days. α-Tocopherol stabilized the membrane-bound lipids against metmyoglobin/H(2)O(2)-initiated oxidation and also significantly (p < 0·05) improved the oxidative stability of rendered fat.

Influence of oxidised dietary oil and antioxidant supplementation on membrane-bound lipid stability in broiler meat.

1. The effects of oxidised oil, dietary alpha-tocopherol and BHA/BHT-supplementation on the fatty acid composition of mitochondrial, microsomal and soluble protein fractions of broiler muscles, and on their lability to metmyoglobin/hydrogen peroxide-catalysed peroxidation were investigated. 2. Oxidised oil in the broiler diets induced rapid oxidation of the membrane-bound lipids and decreased their stability towards metmyoglobin-hydrogen peroxide-catalysed peroxidation. 3. Supplementation of the broiler diets with alpha-tocopherol increased the alpha-tocopherol concentrations in the microsomal and soluble protein fractions of the dark meat as well as the soluble protein fraction of the white meat. This, in turn, stabilised the membrane-bound lipids against metmyoglobin/hydrogen peroxide-initiated peroxidative changes.

Effects of oxidised dietary oil and antioxidant supplementation on broiler growth and meat stability.

1. Broilers were fed on diets containing oxidised sunflower oil, sunflower oil and sunflower oil supplemented with alpha-tocopherol, butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT). 2. Oxidised oil caused a significant reduction in broiler body and carcase weights, whereas alpha-tocopherol and BHA/BHT supplementation improved growth. 3. Meat samples from these broilers were stored at 4 degrees C and -20 degrees C and their oxidative stability evaluated. Feeding oxidised oil to broilers resulted in meat that underwent rapid oxidative changes during refrigerated and frozen storage. 4. On the other hand, dietary alpha-tocopherol and BHA/BHT supplementation increased alpha-tocopherol and BHA/BHT concentrations in meat and significantly (P less than 0.05) improved the oxidative stability of meat during refrigerated and frozen storage.

Further factors influencing N-nitrosamine formation in bacon.

The possible relationship of unsaturated fatty acids in adipose tissue to the formation of N-nitrosamines in bacon was evaluated by trials in which pigs were fed regular (control), tallow-, coconut fat- and corn oil-supplemented diets. Bacon prepared from pigs fed corn oil-supplemented diets contained significantly higher levels of N-nitrosopyrrolidine and N-nitrosodimethylamine than did control bacon samples; however, bacon produced from pigs fed a coconut fat-supplemented diet contained significantly lower levels of N-nitrosopyrrolidine. Fatty acid analyses of the adipose tissue of the bacon samples indicated that N-nitrosopyrrolidine levels in bacon correlated well with the degree of unsaturation of the adipose tissue. N-nitrosothiazolidine was detected in both brine-cured and dry-cured bacon at levels generally below 4 micrograms/kg. However, its formation was greatly reduced by the inclusion of alpha-tocopherol in the cure. The role of woodsmoke in N-nitrosothiazolidine formation in bacon is discussed.