The rising use of natural products creates an imperative need for an enhanced awareness of the safety of current and new products making their way into the marketplace. An important example is natural products containing lignans as the principal active component. Despite their structural similarity the lignan of creosote bush can cause hepato- and renal toxicity while the lignans of flaxseed have no reported serious toxicity. This dissertation aimed to investigate the oxidative metabolism of such lignans to determine whether reversible, competitive interactions and/or bioactivation may explain the differences in their apparent toxicity.<p> The first objective was to study the metabolism and bioactivation of nordihydroguaiaretic acid (creosote bush) and secoisolariciresinol (flaxseed). Nordihydroguaiaretic acid metabolism in rat liver microsomes led to the production of three glutathione adducts formed via ortho¬-quinone reactive intermediates. This metabolism was independent of NADPH and thus attributed to autoxidation. Secoisolariciresinol metabolism yielded lariciresinol and no glutathione adducts suggesting an absence of bioactivation to reactive quinone intermediates.<p> The second objective was to study the autoxidation of nordihydroguaiaretic acid. The major autoxidation product was a unique, stable schisandrin-like cyclolignan which was the result of nordihydroguaiaretic acid cyclization. The half-life of nordihydroguaiaretic acid in aqueous solution, pH 7.4, 37ºC is 3.14 hours suggesting the cyclolignan may be responsible for some of the biological effects of nordihydroguaiaretic acid.<p> The third objective was to study the inhibition of cytochrome P450 isoforms 1A2, 2B, 2C11 and 3A by lignans derived from creosote bush and flaxseed. None of the lignans caused irreversible inhibition. Both creosote bush and flaxseed lignans caused reversible inhibition of P450 enzyme activity that involved competitive or mixed-type inhibition, however the inhibition was present at nonphysiologically relevant concentrations. Activation of cytochrome P450 isoforms was also observed at low lignan concentrations. The results suggest that P450-mediated bioactivation or reversible inhibition cannot explain the differences in toxicity noted between the lignans of creosote bush and flaxseed.<p> This work suggests a minimal risk for drug-lignan interactions at P450 enzymes. Further studies are warranted to determine the presence and biological and toxicological role of the nordihydroguaiaretic acid cyclolignan in herbal preparations.

The physiological benefits of flaxseed against pathological disturbances, such as cancers and heart diseases, are mainly attributed to its high lignan content. This study (Experiment 1) examined the application of pressurized low polarity water (PLPW) for extraction of lignans, proteins and carbohydrates from defatted flaxseed meal. Key processing conditions included temperature (130, 160, 190°C), solvent pH (4, 6.5 and 9), solvent to solid ratio (S/S) (90, 150 and 210 mL/g) and introduction of co-packing material (0 and 3 g glass beads). The addition of 3 g glass beads as co-packing material facilitated extraction by enhancing surface contact between the liquid and solid thus shortening extraction time. Elevated temperature accelerated the extraction rate by increasing the solid diffusion coefficient thereby reducing the extraction time. The maximum yield of lignans (99 %) was obtained at temperatures ranging from 160°C to 190°C, with solvent volume of 180 mL (90 mL/g meal) at pH 9. Optimal conditions for protein extraction (70 %) were pH 9, extraction volume of 420 mL (210 mL/g meal) and 160°C. Total carbohydrates yield was maximized at 50% recovery at pH 4 and 160°C with 420 mL solvent (210 mL/g meal). Increased temperature accelerated extraction, thus reducing solvent volume and time to reach equilibrium. For the extraction of proteins, however, a temperature of 130-160°C is recommended, as proteins are vulnerable to thermal degradation due to heat decomposition. The effects of flow rate and geometric dimensions for extraction of lignans and other flaxseed meal bioactives were further investigated in Experiment 2, based on the variables optimized in the previous experiment. Defatted flaxseed meal was extracted with pH 9 buffered water with meal to co-packing glass beads ratio of 1:1.5 at 5.2 MPa (750 psi) and 180°C. The aqueous extracts were analyzed for lignan, protein and carbohydrate using HPLC and colorimetric methods. The optimal extraction yields for lignan, protein and carbohydrate were found at flow rates of 1 to 2 mL/min with bed depth between 20 and 26 cm and a S/S ratio of 40 to 100 mL/g. The combination of low flow rate and high bed depth allowed the use of lower S/S ratio with reduced total solvent volume consumption. This study also evaluated the mass transfer kinetics governing the process of lignan extraction from flaxseed meal in a fixed bed extraction cell. Diffusion of solute into the continuously flowing solvent was mainly responsible for the mass transfer mechanism as flow rate did not increase proportionally with the yield and rate of extraction. The extraction kinetics were studied on the basis of two approaches: Fick’s diffusion equation and a two-site exponential kinetic model. The proposed two-site exponential kinetic model corresponding to the two-stage extraction (rapid and slow phases) successfully described the experimental data. Diffusivities attained from Fick’s diffusion model ranged from 2 x 10-13 to 9 x 10-13 m2s-1 while mass transfer coefficients were between 4.5 x 10-8 and 2.3 x 10-7 ms-1 for extraction of lignans at 180°C, pH 9 with 1:1.5 meal to co-packing material ratio. / February 2007

The major objectives of this study were to investigate the antioxidant properties of flaxseed lignans secoisolariciresinol (SECO 2) and secoisolariciresinol diglycoside (SDG 1) and their major oxidative compounds using 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH 47) in an in vitro model of lipid peroxidation. This investigation was facilitated by the structural elucidation of the major oxidative compounds and the ability of flaxseed lignans to delay the onset of oxidation in two model systems. <p>This study showed that SECO 2 oxidation occurs at the aromatic (4-OH) and aliphatic (9-OH) hydroxyl groups. Conversely for SDG 1, only compounds derived from the oxidation of aromatic hydroxyl groups were obtained because the 9-OH position is glucosylated. <p>SECO 2 oxidation with AAPH 47 showed that the intermediate 2a is most likely involved in the generation of early-forming (48 and 52) and 2c for the formation of late-forming (49, 50 and 51) oxidation compounds. Compound 48 is formed from dimerization of 2a that is converted to 52 and then to 51. Compound 50 was formed by the addition of a carbon-centre free radical of AAPH (AP radical) to 2c. Compounds 50 and 51 trap carbon-centered AP radicals supporting SECO 2 as a chain-breaking antioxidant and AAPH 47 as a proper model for study of SECO 2 oxidation in vitro. <p>SDG 1 oxidation with AAPH 47 indicated that intermediates 1b and 1c are most likely involved for the formation of early forming compounds (55 and 58) and 1a leads to the late forming compounds (56 and 57). Compound 55 is a result of dimerization. Compound 56 may be directly formed via intermediate radical 1a by adding AP free radicals. Compound 56 was a stable non-radical compound that could trap AP free radicals, thereby supporting SDG 1 as a chain-breaking antioxidant. Hydrogen abstraction from 4-hydroxyl yielded the radical 1a and hydroxyl radical addition to 1a yielded 57. Compound 58 formed from the addition of OH or H2O to 1c. <p>This study demonstrated that AAPH 47 produces carbon-centred AP radicals upon thermal decomposition and mimics the formation of lipid peroxyl radicals. Interaction of carbon-centred AP radicals with SECO 2 and SDG 1 provides a good model to study the antioxidant reactions of SECO 2 in vitro. p*The relative antioxidant capacity of the flaxseed lignans versus BHT 17, in two model systems, was determined. The stoichiometric ratio for SECO 2 and SDG 1 were 1.5 and 1.1-1.2, respectively, compared to BHT 17 (2.0). The induction time by Rancimat analyzer measured inhibition of autoxidation mediated by flaxseed lignans SECO, SDG and SDG polymer in comparison with BHT 17. The induction time data demonstrated that SECO 2 protected canola oil better than either SDG 1 or SDG polymer 3. <p>These results are important for better understanding about the chemistry behind flaxseed lignan antioxidant activities. This study provided useful evidence that flaxseed lignans can be used as natural antioxidants.

The rising use of natural products creates an imperative need for an enhanced awareness of the safety of current and new products making their way into the marketplace. An important example is natural products containing lignans as the principal active component. Despite their structural similarity the lignan of creosote bush can cause hepato- and renal toxicity while the lignans of flaxseed have no reported serious toxicity. This dissertation aimed to investigate the oxidative metabolism of such lignans to determine whether reversible, competitive interactions and/or bioactivation may explain the differences in their apparent toxicity.<p> The first objective was to study the metabolism and bioactivation of nordihydroguaiaretic acid (creosote bush) and secoisolariciresinol (flaxseed). Nordihydroguaiaretic acid metabolism in rat liver microsomes led to the production of three glutathione adducts formed via ortho¬-quinone reactive intermediates. This metabolism was independent of NADPH and thus attributed to autoxidation. Secoisolariciresinol metabolism yielded lariciresinol and no glutathione adducts suggesting an absence of bioactivation to reactive quinone intermediates.<p> The second objective was to study the autoxidation of nordihydroguaiaretic acid. The major autoxidation product was a unique, stable schisandrin-like cyclolignan which was the result of nordihydroguaiaretic acid cyclization. The half-life of nordihydroguaiaretic acid in aqueous solution, pH 7.4, 37ºC is 3.14 hours suggesting the cyclolignan may be responsible for some of the biological effects of nordihydroguaiaretic acid.<p> The third objective was to study the inhibition of cytochrome P450 isoforms 1A2, 2B, 2C11 and 3A by lignans derived from creosote bush and flaxseed. None of the lignans caused irreversible inhibition. Both creosote bush and flaxseed lignans caused reversible inhibition of P450 enzyme activity that involved competitive or mixed-type inhibition, however the inhibition was present at nonphysiologically relevant concentrations. Activation of cytochrome P450 isoforms was also observed at low lignan concentrations. The results suggest that P450-mediated bioactivation or reversible inhibition cannot explain the differences in toxicity noted between the lignans of creosote bush and flaxseed.<p> This work suggests a minimal risk for drug-lignan interactions at P450 enzymes. Further studies are warranted to determine the presence and biological and toxicological role of the nordihydroguaiaretic acid cyclolignan in herbal preparations.

The objectives of our study were to determine the potential of 1H MRS in detecting (1) early colonic inflammation, (2) effects of various fatty acids on normal colon and (3) their effects on IBD. Sprague dawley rat fed with 2% carrageenan was used as a model of IBD. Flaxseed oil served as ω-3, corn oil as ω-6 and beef tallow as saturated fatty acid sources. Control group animals were fed 5% corn oil, whereas, those in high-fat diet groups received an additional 7% of the respective fatty acids. After 2 weeks, 1H MRS and histology were conducted on excised colonic mucosa. Statistical classification strategy (SCS) used for analyzing 1H MRS data achieved an accuracy of 82 % in stage 1, 90-100% in stage 2 and 96-100% in stage 3. This implies that 1H MRS is a sensitive tool to diagnose early IBD and the effects of dietary fat on IBD.

The physiological benefits of flaxseed against pathological disturbances, such as cancers and heart diseases, are mainly attributed to its high lignan content. This study (Experiment 1) examined the application of pressurized low polarity water (PLPW) for extraction of lignans, proteins and carbohydrates from defatted flaxseed meal. Key processing conditions included temperature (130, 160, 190°C), solvent pH (4, 6.5 and 9), solvent to solid ratio (S/S) (90, 150 and 210 mL/g) and introduction of co-packing material (0 and 3 g glass beads). The addition of 3 g glass beads as co-packing material facilitated extraction by enhancing surface contact between the liquid and solid thus shortening extraction time. Elevated temperature accelerated the extraction rate by increasing the solid diffusion coefficient thereby reducing the extraction time. The maximum yield of lignans (99 %) was obtained at temperatures ranging from 160°C to 190°C, with solvent volume of 180 mL (90 mL/g meal) at pH 9. Optimal conditions for protein extraction (70 %) were pH 9, extraction volume of 420 mL (210 mL/g meal) and 160°C. Total carbohydrates yield was maximized at 50% recovery at pH 4 and 160°C with 420 mL solvent (210 mL/g meal). Increased temperature accelerated extraction, thus reducing solvent volume and time to reach equilibrium. For the extraction of proteins, however, a temperature of 130-160°C is recommended, as proteins are vulnerable to thermal degradation due to heat decomposition. The effects of flow rate and geometric dimensions for extraction of lignans and other flaxseed meal bioactives were further investigated in Experiment 2, based on the variables optimized in the previous experiment. Defatted flaxseed meal was extracted with pH 9 buffered water with meal to co-packing glass beads ratio of 1:1.5 at 5.2 MPa (750 psi) and 180°C. The aqueous extracts were analyzed for lignan, protein and carbohydrate using HPLC and colorimetric methods. The optimal extraction yields for lignan, protein and carbohydrate were found at flow rates of 1 to 2 mL/min with bed depth between 20 and 26 cm and a S/S ratio of 40 to 100 mL/g. The combination of low flow rate and high bed depth allowed the use of lower S/S ratio with reduced total solvent volume consumption. This study also evaluated the mass transfer kinetics governing the process of lignan extraction from flaxseed meal in a fixed bed extraction cell. Diffusion of solute into the continuously flowing solvent was mainly responsible for the mass transfer mechanism as flow rate did not increase proportionally with the yield and rate of extraction. The extraction kinetics were studied on the basis of two approaches: Fick’s diffusion equation and a two-site exponential kinetic model. The proposed two-site exponential kinetic model corresponding to the two-stage extraction (rapid and slow phases) successfully described the experimental data. Diffusivities attained from Fick’s diffusion model ranged from 2 x 10-13 to 9 x 10-13 m2s-1 while mass transfer coefficients were between 4.5 x 10-8 and 2.3 x 10-7 ms-1 for extraction of lignans at 180°C, pH 9 with 1:1.5 meal to co-packing material ratio.

The objectives of our study were to determine the potential of 1H MRS in detecting (1) early colonic inflammation, (2) effects of various fatty acids on normal colon and (3) their effects on IBD. Sprague dawley rat fed with 2% carrageenan was used as a model of IBD. Flaxseed oil served as ω-3, corn oil as ω-6 and beef tallow as saturated fatty acid sources. Control group animals were fed 5% corn oil, whereas, those in high-fat diet groups received an additional 7% of the respective fatty acids. After 2 weeks, 1H MRS and histology were conducted on excised colonic mucosa. Statistical classification strategy (SCS) used for analyzing 1H MRS data achieved an accuracy of 82 % in stage 1, 90-100% in stage 2 and 96-100% in stage 3. This implies that 1H MRS is a sensitive tool to diagnose early IBD and the effects of dietary fat on IBD.

The physiological benefits of flaxseed against pathological disturbances, such as cancers and heart diseases, are mainly attributed to its high lignan content. This study (Experiment 1) examined the application of pressurized low polarity water (PLPW) for extraction of lignans, proteins and carbohydrates from defatted flaxseed meal. Key processing conditions included temperature (130, 160, 190°C), solvent pH (4, 6.5 and 9), solvent to solid ratio (S/S) (90, 150 and 210 mL/g) and introduction of co-packing material (0 and 3 g glass beads). The addition of 3 g glass beads as co-packing material facilitated extraction by enhancing surface contact between the liquid and solid thus shortening extraction time. Elevated temperature accelerated the extraction rate by increasing the solid diffusion coefficient thereby reducing the extraction time. The maximum yield of lignans (99 %) was obtained at temperatures ranging from 160°C to 190°C, with solvent volume of 180 mL (90 mL/g meal) at pH 9. Optimal conditions for protein extraction (70 %) were pH 9, extraction volume of 420 mL (210 mL/g meal) and 160°C. Total carbohydrates yield was maximized at 50% recovery at pH 4 and 160°C with 420 mL solvent (210 mL/g meal). Increased temperature accelerated extraction, thus reducing solvent volume and time to reach equilibrium. For the extraction of proteins, however, a temperature of 130-160°C is recommended, as proteins are vulnerable to thermal degradation due to heat decomposition. The effects of flow rate and geometric dimensions for extraction of lignans and other flaxseed meal bioactives were further investigated in Experiment 2, based on the variables optimized in the previous experiment. Defatted flaxseed meal was extracted with pH 9 buffered water with meal to co-packing glass beads ratio of 1:1.5 at 5.2 MPa (750 psi) and 180°C. The aqueous extracts were analyzed for lignan, protein and carbohydrate using HPLC and colorimetric methods. The optimal extraction yields for lignan, protein and carbohydrate were found at flow rates of 1 to 2 mL/min with bed depth between 20 and 26 cm and a S/S ratio of 40 to 100 mL/g. The combination of low flow rate and high bed depth allowed the use of lower S/S ratio with reduced total solvent volume consumption. This study also evaluated the mass transfer kinetics governing the process of lignan extraction from flaxseed meal in a fixed bed extraction cell. Diffusion of solute into the continuously flowing solvent was mainly responsible for the mass transfer mechanism as flow rate did not increase proportionally with the yield and rate of extraction. The extraction kinetics were studied on the basis of two approaches: Fick’s diffusion equation and a two-site exponential kinetic model. The proposed two-site exponential kinetic model corresponding to the two-stage extraction (rapid and slow phases) successfully described the experimental data. Diffusivities attained from Fick’s diffusion model ranged from 2 x 10-13 to 9 x 10-13 m2s-1 while mass transfer coefficients were between 4.5 x 10-8 and 2.3 x 10-7 ms-1 for extraction of lignans at 180°C, pH 9 with 1:1.5 meal to co-packing material ratio.

This diploma thesis deals with theme "Quality evaluation of gluten-free food, concretely gluten-free pastries". Theoretical part is concerned about coeliac disease in general, their symptoms, forms and diagnostic. There is described basic principal of coeliac disease and approachable gluten-free food. Then the basics of sensory analyse are described. Practical part is focused on finding suitable gluten-free flour and baking samples of bread based on recipe with care about improving nutritional value. Baked bread samples, made from commixture of gluten-free flour with enrichment of different amount of flaxseed, were evaluated with suitable methods of sensory analysis. This analyse shows which sample is the most preferred and based on those information it is proposed to enlarge offer in gluten-free pastry.

LIMA, Cândice Camelo. Aplicação das Farinhas de Linhaça (Linum usitatissimum L.) e Maracujá (Passiflora edulis Sims f. flavicarpa Deg.) no Processamento de Pães com Propriedades Funcionais. 2007. 148 f. : Dissertação (mestrado) - Universidade Federal do Ceará, Centro de Ciências Agrárias, Departamento de Tecnologia de Alimentos, Fortaleza-CE, 2007 / Submitted by Nádja Goes (nmoraissoares@gmail.com) on 2016-06-01T12:41:18Z No. of bitstreams: 1 2007_dis_cclima.pdf: 988233 bytes, checksum: 61b6ebae5003a46d0973ccc4ede61a5b (MD5) / Approved for entry into archive by Nádja Goes (nmoraissoares@gmail.com) on 2016-06-01T12:42:36Z (GMT) No. of bitstreams: 1 2007_dis_cclima.pdf: 988233 bytes, checksum: 61b6ebae5003a46d0973ccc4ede61a5b (MD5) / Made available in DSpace on 2016-06-01T12:42:36Z (GMT). No. of bitstreams: 1 2007_dis_cclima.pdf: 988233 bytes, checksum: 61b6ebae5003a46d0973ccc4ede61a5b (MD5) Previous issue date: 2007 / In the last decades, there is a growing in the interest research and consume foods product with functional properties. This happening due the public knowledge of these product’s benefits. The flaxseed (Linum usitatissimun L.) has been considerated a functional ingredient of great importance. This importance is due its functional combinations such as linolenic acid, lignans and fibers that are potentially beneficial to our health. Several researches evidence the positive effects of adding flaxseed to the food to the combat and prevention of many diseases, for example: cancer, constipation, menopause, disease cardiovascular, among others. The passion fruit flour has demonstrated its ability to reduce the bad cholesterol (LDL) and to increase the good cholesterol (HDL). Therefore, the passion fruit flour has been pointed out as an auxiliary in the treatment of diabetes and weight reduction. Thus, this research work has the purpose of developing bread with functional characteristics. We have formulated four experiments. The first one, the standard bread (FP), without the addition of flaxseed and passion fruit flour. In the other three experiments have received 3% of fiber food (fruit passion flour) and additionally 4% (FML4), 7% (FML7) and 10% (FML10) of flaxseed flour. The experiments were evaluated over their physic, chemical, physic-chemical, sensorial, microbiological and rheologic characteristics. They were put under sensorial tests to prove the global acceptance, acceptance for the attributes of purchasing intention. The data were statically investigated through descriptive analysis and variance analysis (ANOVA) and the Tukey test for comparison of the averages, using the significance level of 5% (p≤0,05). The most noteworthy modifications in the composition of the bread that were added flaxseed flour were verified into values of proteins, lipids, calories, fibers and carbohydrates. The acceptability of the bread was evaluated by 60 volunteers by the attribution of flavor, taste, texture, residual taste, smoothness, and general reception and purchase intention. These evaluations were made by hedonic scale and the ideal scale to value aroma, taste, texture and residual taste. All analyzed results had received hedonics values in the range and a global acceptance. The outcome of purchasing intention suggested that the volunteers have shown more interest to the bread FML4 and FML7. The addition of flaxseed flour and passion fruit flour has promoted a significant increase on the fiber amount, turning the bread with high amount of fiber food / Os benefícios do consumo de produtos alimentícios com propriedades funcionais vêm aumentando e desenvolvendo interesse nas últimas décadas em muitos pesquisadores e consumidores. A linhaça (Linum usitatissimum L.) tem sido considerada um ingrediente funcional de grande importância por conter combinações funcionais como o ácido linolênico (ALA), lignanas e fibras. Diversas pesquisas evidenciam os efeitos positivos da alimentação acrescentada com linhaça no tratamento e prevenção de muitas enfermidades como: doenças cardiovasculares, câncer, artrite, sintomas indesejáveis da menopausa, constipação, entre outras. A farinha do maracujá vem demonstrando possuir a capacidade de reduzir o chamado “mau colesterol” (LDL) e aumentar o “bom colesterol” (HDL), sendo indicada como auxiliar no tratamento do diabetes e redução de peso. Assim este trabalho teve como objetivo desenvolver um produto de panificação com características funcionais. Foram elaboradas quatro formulações de pão de forma, sendo uma formulação padrão, sem adição das farinhas de linhaça e maracujá (FP) e três substituindo-se parcialmente a farinha de trigo por percentuais de farinha de linhaça 4% (FML4), 7% (FML7) e 10% (FML10), e todas com adição de 3% de fibra alimentar (farinha de maracujá). As amostras foram avaliadas quanto às suas características físicas, químicas, físico-químicas, reológicas, sensoriais e microbiológicas. Foram submetidos a testes sensoriais de aceitação global, aceitação por atributos e intenção de compra. Os dados foram analisados estatisticamente através de análise descritiva, análise de variância (ANOVA) e teste de Tukey para comparação das médias, utilizando nível de significância de 5% (p≤0,05). As modificações mais significativas na composição dos pães com adição de farinha de linhaça e farinha de maracujá foram verificadas nos teores de proteínas, lipídios, carboidratos, fibras e valores calóricos. A aceitabilidade dos pães foi avaliada por 60 provadores, quanto ao aroma, textura, sabor, sabor residual, aceitação geral e intenção de compra através da escala hedônica e escala do ideal para avaliar aroma, maciez, sabor e sabor residual. Todas as formulações analisadas receberam valores hedônicos na faixa e aceitação em todas as variáveis. Os resultados de intenção de compra sugeriram que os consumidores tiveram maior interesse nos pães FML4 e FML7. A adição da farinha de linhaça e farinha de maracujá provocou aumento significativo nos teores de fibras, tornando os pães com alto teor de fibra alimentar