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Antioxidant Effects of Phenolic Rye ( Secale cereale L.) Extracts, Monomeric Hydroxycinnamates, and Ferulic Acid Dehydrodimers on Human Low-Density Lipoproteins
Abstract
Dietary antioxidants that protect low-density lipoprotein (LDL) from oxidation may help to prevent atherosclerosis and coronary heart disease. The antioxidant activities of purified monomeric and dimeric hydroxycinnamates and of phenolic extracts from rye (whole grain, bran, and flour) were investigated using an in vitro copper-catalyzed human LDL oxidation assay. The most abundant ferulic acid dehydrodimer (diFA) found in rye, 8-O-4-diFA, was a slightly better antioxidant than ferulic acid and p-coumaric acid. The antioxidant activity of the 8-5-diFA was comparable to that of ferulic acid, but neither 5-5-diFA nor 8-5-benzofuran-diFA inhibited LDL oxidation when added at 10-40 microM. The antioxidant activity of the monomeric hydroxycinnamates decreased in the following order: caffeic acid > sinapic acid > ferulic acid > p-coumaric acid. The antioxidant activity of rye extracts was significantly correlated with their total content of monomeric and dimeric hydroxycinnamates, and the rye bran extract was the most potent. The data suggest that especially rye bran provides a source of dietary phenolic antioxidants that may have potential health effects.
... Dans la majorité des cas (au moins 90%), il s'agit d'un diabète de type 2, il se manifeste sous forme de véritable « épidémie silencieuse ». Il a de graves conséquences en termes de morbidité, de mortalité et de prise en charge médicale très coûteuse [2]. ...
... Les quatre principaux acides phénoliques du son de seigle sont : l'acide caféique, l'acide sinapique, l'acide férulique et le p-coumarique. L'acide férulique constitue le principal acide phénolique du son de seigle [2]. Il est reconnu par son potentiel antioxydant en empêchant l'oxydation du LDL-cholestérol [2,45]. ...
... L'acide férulique constitue le principal acide phénolique du son de seigle [2]. Il est reconnu par son potentiel antioxydant en empêchant l'oxydation du LDL-cholestérol [2,45]. ...
Le son représente l'enveloppe externe qui est une partie importante des grains du seigle, du fait de son intérêt nutritionnel et thérapeutique. L'étude portée sur la composition chimique montre que le son est une source riche en fibres avec un taux estimé à 39%. Ce travail porte sur la recherche de l'effet hypoglycémiant, hypolipidémiant et l'évaluation du pouvoir antioxydant après avoir administré un régime expérimental à base de son de seigle aux rats nor-maux et d'autres rendus diabétiques par la streptozotocine (STZ) pendant un mois d'expérimentation. Cet effet est éga-lement analysé chez les rats normaux et diabétiques soumis à un régime témoin. D'autres paramètres le poids corporel, le poids de fèces et la teneur en protéines totales, ont été éva-lués. Les résultats ont montré un effet hypoglycémiant net. De même on a noté l'influence du son de seigle (riche en fibres) sur la diminution de la concentration du cholestérol et des triglycérides. L'évaluation du statut antioxydant a montré des teneurs élevées des vitamines E et C et de l'ORAC chez nos lots expérimentaux et une diminution des marqueurs de la peroxydation lipidique et protéique. Mots clés Son de seigle · Effet hypoglycémiant · Effet hypolipidémiant · Stress oxydatif · Fibres alimentaires Abstract The bran of secale represents the external envelope , an important part of the grains of rye because of its nutritional and therapeutic interest. The study carried on the chemical composition of the bran of rye, watch which the bran is a source rich in fibers with an important rate estimated at 39%. This work concerns the research of the hypoglycemia effect, correct lipidic metabolic disorders and the evaluation of the antioxidant capacity, after having managed an experimental mode containing bran of rye to the normal rats and others returned diabetics during 1 month of experimentation. This effect is also analyzed in the normal rats and diabetics subjected to a pilot mode. Other parameters the body weight, the weight of deposit and the content of total proteins were evaluated. The research of the hypogly-cemia effect of the bran of rye, led us to results showing an hypoglycemia effect. The same our results show as the influence of rye fibers on the disorders of the lipidic metabolism is significant in the reduction in the concentration of cholesterol and triglycerides. The evaluation of the antioxi-dant statute showed high contents of the vitamins E, C and total antioxidant capacity (ORAC) at our experimental rats and a reduction of a markers of lipidic and proteinic oxidation.
... Fatty acids have anticoagulant, antihypertensive, hypocholestero-lemic, antioxidant, neuroprotective, cardioprotective, antiinflammatory action, regulate lipid metabolism, improve the conduction of nerve impulses, and promote more efficient brain cells. Some scientists suggest an important role of PUFA in the prevention of various cancers [2,8]. ...
... For example, barley contains β-dglucan, tocopherols, tocotrienols and phenols (proanthocyanidins, flavonols, flavones, chalcones, quinones and derivatives of benzoic and cinnamic acids). Beta-dglucan plays a significant role in prophylaxis of diabetes, cardiovascular disease, hypertension and others according to research results [8,9]. ...
... Secale cereale L. grain is rich in dietary fibre, phenolic compounds (polyphenols, flavonoids, phenolic acids (p-coumaric, ferulic, synaptic acids), thiols and sterols. Phenolic compounds act as antioxidants and, accordingly, reduce the risk of cancer, cardiovascular diseases, etc. [8,10]. Also, rye grain is rich in unsaturated fatty acids, namely oleic, linoleic and linolenic. ...
Introduction. Sowing rye (Secale cereale L.) and common barley (Hordéum vulgáre L.) are annual herbaceous plants of the Poaceae family, they are widely cultivated in many countries around the world as cereals and fodder crops. Sufficient raw material base of sowing rye and barley makes them promising sources for new drugs. Materials and methods. The fatty acid composition in lipophilic fractions of seeds, stems and leaves of sowing (Khamarka variety) and common barley (Shedevr variety) was studied by gas chromatography. Results. As a result of the study, the quantitative content of 14 fatty acids in the stems and leaves of barley, 13 – in the leaves of rye and 12 – in the stems of rye and in both types of studied seeds was identified and established. In all types of the studied raw materials, unsaturated fatty acids were quantitatively predominant, the content of which prevailed in seeds of rye – 82.89 % and barley – 76.35 %. In stems of common barley their content was 64.04 %, leaves of common barley – 66.31 % of the amount. In stems and leaves of rye, the predominance of unsaturated fatty acids over saturated ones was insignificant: 49.00 % vs. 47.05 % and 53.70 % vs. 43.03 %, respectively. Among the unsaturated fatty acids, linoleic and linolenic acids dominated. Palmitic acid predominated among the saturated raw materials in all types of studied raw materials Conclusions. Quantitative content of fatty acids in seeds, stems and leaves of sowing rye (Khamarka variety) and common barley (Shedevr variety) was identified and established by gas chromatography. The results of the research indicate a rich fatty acid composition of the studied raw materials and can be used to create drugs based on them
... Phytosterols are important micronutrients, which cannot be synthesized by the human body, often added to orange juice, low-fat yogurt, chocolate and milk as dietary supplements to ensure human health (Andreasen et al., 2001;Zhang et al., 2022). Phytosterol esters are the forms of phytosterols present in natural plants, accounting for approximately 30-80% of the total sterol content, and are mostly distributed in grain and plant seeds, such as soybean, olive, cotton seed, lotus seed, coconut, safflower, and peanut oil (Broughton and Beaudoin, 2021;Cercaci et al., 2003;Flakelar et al., 2017). ...
... As naturally abundant phenolic acids, vanillic acid, protocatechuic acid, and sinapic acid have been comprehensively studied. These three phenolic acids are naturally enriched in grain, fruits and vegetables and provide cytoprotection (Andreasen et al., 2001;Dhar et al., 2007;Juurlink et al., 2014;Tan and Shahidi, 2013). In particular, they work synergistically with phytosterols to inhibit lipid peroxidation, regulate the lipids profile, endoplasmic reticulum stress response, and mitochondrial function in cells (Ashokkumar and Vinothiya, 2023;He et al., 2018;Mohan et al., 2023). ...
... Sinapic Acid (SA) is a polyphenol (3,5-Dimethoxy-4-Hydroxycinnamic acid, Figure 1), the main phytoconstituent plentifully present in plants of family Brassicaceae, citrus berry fruits, vegetables, cereals, and oil-seed crops that are commonly consumed as food and beverages [13]. It is very famous for its potent chemopreventive biological effects, antioxidant, antihypertensive, antidiabetic, anti-inflammatory, anti-anxiety, gastro protective, hepatoprotective, and neuroprotective effects [8,[13][14][15][16][17][18][19]. ...
... Sinapic Acid (SA) is a polyphenol (3,5-Dimethoxy-4-Hydroxycinnamic acid, Figure 1), the main phytoconstituent plentifully present in plants of family Brassicaceae, citrus berry fruits, vegetables, cereals, and oil-seed crops that are commonly consumed as food and beverages [13]. It is very famous for its potent chemopreventive biological effects, antioxidant, antihypertensive, antidiabetic, anti-inflammatory, anti-anxiety, gastro protective, hepatoprotective, and neuroprotective effects [8,[13][14][15][16][17][18][19]. In rodent models, oral or systemic administration of phenolic acids such as epigallocatechin gallate, resveratrol, quercetin, and curcumin downregulate nuclear factor (NF-κ B)-dependent gene expression and upregulate phase II detoxifying and antioxidant proteins. ...
Background: Ulcerative colitis (UC) is a long-term condition which results in inflammation and ulcers of the colon and rectum. The key indications of active disease are abdominal pain and diarrhea mixed with blood. Aims: We explore the underlying colon protective mechanism of sinapic acid (SA) against acetic acid (AA) induced ulcerative colitis in rats. The implications of inflammation, oxidative stress, and apoptosis are studied. Methodology: Twenty-four rats were distributed into four categories, normal control (NC), ulcerative colitis (UC), ulcerative Colitis with SA 40 mg/kg (SA 40 mg/kg + AA), and ulcerative colitis with prednisolone (PRDL 10 mg/kg + AA), and were pretreated orally with saline, saline and SA (40 mg/kg/day) or PRDL (10 mg/kg/day) respectively, for 7 days. UC was prompted by trans-rectal administration of 4% AA on the 5th day, colon tissues were surgically removed for gross morphology and histological inspection, oxidative stress, and inflammatory markers and immunoblot analysis of Bax, caspase-3, and Bcl-2. Results: Macroscopic and histological inspection demonstrated that both SA 40 mg/kg and PRDL (10 mg/kg/day) significantly ameliorates colonic injuries. In addition, both pretreatments significantly ameliorates AA-induced UC, oxidative stress, as indicated by suppressed malondialdehyde (MDA), nitric oxide (NO) levels and restoring antioxidant/oxidant balance as indicated by catalase and glutathione levels, suppressed inflammation via inhibiting cytokines TNF-α, IL-6, inflammatory markers MPO, PGE2, COX-2 and NF-κB and inhibiting the protein expression of Bax and caspase-3 apoptotic protein and increasing the anti-apoptotic protein, Bcl-2 thereby inhibiting apoptosis. Conclusion: Sinapic acid significantly ameliorates AA induced UC in rats by suppressing inflammation, oxidative stress, and apoptosis in colonic tissues which exhibits its potential for the management of UC.
... Research has been conducted for many years related to dietary fibers and their effects on the human body. They have the potential to reduce low-density cholesterol [18], to minimize the risk associated with diseases such as coronary heart disease, diabetes mellitus, and obesity, and also dietary fiber can improve intestinal peristalsis, which has a beneficial effect on the entire gastrointestinal tract [19,20]. Regarding the differentiation of fiber into soluble and insoluble fiber, some differences have also been found in their effects on the body: soluble dietary fiber has immunomodulatory and anti-inflammatory effects, while insoluble fiber stimulates the intestine, being the main source of energy for its microbiota [21][22][23]. ...
Spent grain is a component of grain that consists primarily of its shells and is a by-product of the production of beer or ethyl alcohol. It is characterized by a diverse chemical composition, mainly composed of proteins and dietary fibers and, to a lesser extent, lipids, minerals, phenolic compounds, as well as B vitamins and vitamin E. In its native form, it is a product with a high moisture content, which makes it unsuitable for long-term storage. In this connection, several problems arise that worsen the economic and environmental situation at the global level. This article presents effective methods of processing spent grain to prevent negative consequences associated with its irrational use. Possibilities for the application of used spent grain in the food industry are also presented: bakery and pasta, confectionery, the meat and dairy industry, as well as the production of beverages. Thus, the integration of spent grain in the food composition will lead to solving the economic and environmental difficulties that have appeared in the last decades; it will allow the development of a functional food market, which will lead to the improvement of the quality of the population life by strengthening the trend of good nutrition and reducing the negative impact on the environment.
... During metal stress, phenolic compounds can function as antioxidants, demonstrating the capability to scavenge free radicals, chelate metal ions, and donate electrons or hydrogen atoms. The effectiveness of these actions depends on the structural features, specifically the number and position of the hydroxyl and carboxyl groups, with hydroxycinnamic acids (C6-C3 structure) exhibiting greater antioxidant ability than hydroxybenzoic acids [53,54]. Gallic acid is a potent antioxidant. ...
This study aimed to investigate the response of Populus nigra L. × Populus maximowiczii to the addition of selected metals in soil. Rooted cuttings were planted in pots containing soil enriched with equimolar concentrations of Pb, Zn, Al, Ni, and Cu (500 mL of 4 mM solutions of single metal salts: (Pb(NO3)2; Zn(NO3)2 × 6H2O; Al(NO3)3 × 9H2O; Ni(NO3)2 × 6H2O; or Cu(NO3)2 × 3H2O). Growth parameters, metal accumulation, and physiological and biochemical parameters were assessed after four weeks of cultivation, simulating early response conditions. The results showed diverse metal accumulation in poplar organs, along with an increase in biomass and minor changes in gas exchange parameters or chlorophyll fluorescence. Among low-molecular-weight organic acids, citric and succinic acids were dominant in the rhizosphere, and roots with malonic acid were also present in the shoots. Only p-coumaric acid was found in the phenolic profile of the roots. The shoots contained both phenolic acids and flavonoids, and their profile was diversely modified by particular metals. Sucrose and fructose content increased in shoots that underwent metal treatments, with glucose increasing only in Cu and Al treatments. Principal component analysis (PCA) revealed variations induced by metal treatments across all parameters. Responses to Pb and Zn were partially similar, while Cu, Ni, or Al triggered distinct reactions. The results indicate the adaptation of P. nigra L. × P. maximowiczii to soil containing elevated levels of metals, along with potential for soil remediation and metal removal. However, further studies are needed to evaluate the effect of differences in early responses to particular metals on plant conditions from a long-term perspective.
... Dietary fiber has attracted much attention over the years, due to its potential as a pharmaceutical product because of its ability to lower cholesterol [34], prevent coronary heart diseases and diabetes, prevent the obesity development, and improve intestinal peristalsis, which is particularly relevant to the elderly [35,36]. Dietary fiber is a material that binds potential nutrients, leading to the formation of new metabolites, and may also increase the growth of intestinal villi, increasing the assimilation of substances. ...
This article aimed to review the recent literature on the characterization of dietary fibers and their role in the human body, focusing on the methods of extraction of dietary fibers from agro-food waste as well as their use in various areas of the food industry. Dietary fibers are biologically active substances with beneficial effects on human health. Soluble dietary fiber is involved in reducing cholesterol levels and blood sugar levels, while insoluble dietary fiber helps regulate intestinal transit and maintain colon health. It would be useful to identify the extraction procedures and characterization of dietary fibers from agro-food waste. Fruit waste contains relevant amounts of bioactive compounds, such as: phenolic acids, flavonoids, lignins, carotenoids, etc. In addition, fruit waste contains significant amounts of dietary fiber with nutraceutical important activities, such as modulating the intestinal microbiota, lowering cholesterol, triglycerides and glycemic load in the blood. Hence, obtaining dietary fiber from agro-industrial waste can solve a number of economic and environmental problems that aim reducing waste, increasing the sustainability and profitability of companies in the Republic of Moldova. Dietary fiber can be used in various types of food, such as products of bakery and confectionery, meat, dairy products, and pasta. They can be used as stabilizers with an impact on food texture or ingredients with low caloric value, partially replacing caloric constituents such as fats, starch or sugars. Another important property is the prebiotic effect of dietary fibers. This property is determined by the fact that dietary fibers are indigestible or poorly digestible and are fermented selectively by intestinal microbiota, conferring health benefits to the host.
... Other studies indicate that hydroxycinnamic acids have a higher antioxidant activity than hydroxybenzoic acids, possibly due to the CH=CH-COOH group, which confers a stronger capacity to donate H and neutralize radicals than the -COOH group of hydroxybenzoic acids [60,79]. In the case of flavonoids, the nature of the substitutions on the B and C rings is decisive for their antioxidant activity [80]. ...
In Morocco, the abundance of low-value varieties in the oases may provide an opportunity to capitalize on this richness to create new nutraceutical food products. In this context, the phenolic profile and antioxidant capacity of four Moroccan date varieties were analyzed. Our results indicate that the levels of total polyphenols, total flavonoids and total condensed tannins vary, respectively, from 91.86 to 364.35 mg GAE/100 g of dry weight (DW), 46.59 to 111.80 mg QE/100 g DW and 16.10 to 42.03 mg CE/100 g DW during the 2021 harvest season. Furthermore, during the 2022 harvest season, these contents vary, respectively, from 119.13 to 410.39 mg GAE/100 g DW, 59.30 to 110.85 mg QE/100 g DW and 21.93 to 53.95 mg CE/100 g DW. The results of the HPLCUV-VIS analysis revealed that, in all four varieties, gallic acid was and remained one of the major compounds in the date extracts. In addition, a high antioxidant activity of date extracts was particularly observed in the three tests, namely ferric reducing power (FRAP), ferrous ion chelating capacity (FIC) and the phosphomolybdate test. This richness in phenolic compounds makes lowvalue dates a source of active ingredient that can replace the synthetic antioxidants used in the food and pharmaceutical industries.
... Sinapic acid (SA, 3,5-dimethoxy-4-hydroxycinnamic acid) is a naturally occurring hydroxycinnamic acid, found in plants, fruits, vegetables, several cereals, and oil crops [1][2][3][4] with potential use in food processing, cosmetics, and in the pharmaceutical industry. SA acts as an anti-inflammatory [5], antidiabetic [6], anticancer agent [7] with antioxidant [8], antibacterial [9], chemopreventive [10], neuroprotective [11], and antihypertensive [12] effects. ...
The thermal stability of bovine serum albumin (BSA) in Tris buffer, as well as the effect of sinapic acid (SA) on protein conformation were investigated via calorimetric (differential scanning microcalorimetry—μDSC), spectroscopic (dynamic light scattering—DLS; circular dichroism—CD), and molecular docking approaches. μDSC data revealed both the denaturation (endotherm) and aggregation (exotherm) of the protein, demonstrating the dual effect of SA on protein thermal stability. With an increase in ligand concentration, (i) protein denaturation shifts to a higher temperature (indicating native form stabilization), while (ii) the aggregation process shifts to a lower temperature (indicating enhanced reactivity of the denatured form). The stabilization effect of SA on the native structure of the protein was supported by CD results. High temperature (338 K) incubation induced protein unfolding and aggregation, and increasing the concentration of SA altered the size distribution of the protein population, as DLS measurements demonstrated. Complementary information offered by molecular docking allowed for the assessment of the ligand binding within the Sudlow’s site I of the protein. The deeper insight into the SA–BSA interaction offered by the present study may serve in the clarification of ligand pharmacokinetics and pharmacodynamics, thus opening paths for future research and therapeutic applications.
... On the other hand, the presence of a high protein content is of vital importance for the strengthening and maintenance of the muscles and bones that make up the human body, thus providing a high energy intake [40]. In addition, the high content of crude fiber and carbohydrates in seeds display several benefits, such as the reduction of cholesterol, diabetes, coronary heart disease and even the prevention and/or treatment of obesity [41][42][43], showing the high quality and the potential of these bio-residues as functional ingredients [37]. The obtained results from the approximate analysis are comparable with the results of other researchers [37,[44][45][46][47][48], which found that Prunus seeds were characterized by a protein content of 6-20% (w), a crude fiber content of 15-20% (w), an oil content of 11-57% (w), a moisture content of 5-7% (w), an ash content of 1-3% (w) and a carbohydrate content of 18-27% (w). ...
Citation: Rodríguez-Blázquez, S.; Gómez-Mejía, E.; Rosales-Conrado, N.; León-González, M.E.; García-Sánchez, B.; Miranda, R. Valorization of Prunus Seed Oils: Fatty Acids Composition and Oxidative Stability. Molecules 2023, 28, 7045. https://doi.org/10.3390/ molecules28207045 Academic Editors: Petko Denev, Abstract: Prunus fruit seeds are one of the main types of agri-food waste generated worldwide during the processing of fruits to produce jams, juices and preserves. To valorize this by-product, the aim of this work was the nutritional analysis of peach, apricot, plum and cherry seeds using the official AOAC methods, together with the extraction and characterization of the lipid profile of seed oils using GC-FID, as well as the measurement of the antioxidant activity and oxidative stability using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging method. Chemometric tools were required for data evaluation and the obtained results indicated that the main component of seeds were oils (30-38%, w). All seed oils were rich in oleic (C18:1n9c) and linoleic (C18:2n6c) acids and presented heart-healthy lipid indexes. Oil antioxidant activity was estimated in the range IC 50 = 20-35 mg·mL −1 , and high oxidative stability was observed for all evaluated oils during 1-22 storage days, with the plum seed oil being the most antioxidant and stable over time. Oxidative stability was also positively correlated with oleic acid content and negatively correlated with linoleic acid content. Therefore, this research showed that the four Prunus seed oils present interesting healthy characteristics for their use and potential application in the cosmetic and nutraceutical industries.
... Recently, ferulic acid production from wheat bran has been reported by solid-state fermentation of Aspergillus niger strain FA-WB (Yin et al. 2019). Whereas, sinapic acid is widely found in rye (Andreasen et al. 2001), wheat bran (Arranz and Saura Calixto, 2010), rapeseed and canola seeds (Mayengbam, Aachary, and Thiyam-Holl€ ander 2014), broccoli, kale, cabbage (Yilmaz and Bagci 2018), fruit and spices (Ero glu et al. 2018). ...
... Hydroxycinnamic acids show higher antioxidant activity than hydroxybenzoic acids (Andreasen et al., 2001). The high activity of hydroxycinnamic acid is associated with the presence of a CH=CH-COOH group, which allows radical stabilization and high H-donation compared to the -COOH group in hydroxybenzoic acids (Rice-Evans et al., 1996). ...
... Hydroxycinnamic acids show higher antioxidant activity than hydroxybenzoic acids (Andreasen et al., 2001). The high activity of hydroxycinnamic acid is associated with the presence of a CH=CH-COOH group, which allows radical stabilization and high H-donation compared to the -COOH group in hydroxybenzoic acids (Rice-Evans et al., 1996). ...
... This offers developer the opportunity to improve the nutritional and health enhancing properties. Various studies have already proven that foods having high dietary fibres have potential to reduce blood cholesterol, digestion problems, colon related cancer, ( Marlett et al., 2002) [6,5,16,19,2,49,52,28] , risk of diabetes mellitus (Type 2), coronary heart disease, blood pressure, obesity (Schweizer & W€ursch, 1986;Topping, 1991;Davidson & McDdonald, 1998;Schneeman, 1998;Terry et al., 2001;Wang, Rosell, & de Barber, 2002;Ferguson & Harris, 2003;Peters et al., 2003;Bingham et al., 2003;Cassidy, Bingham and Cummings, 1994;Viertanen and Aro, 1994;Ascherio and Willet, 1995;Kimm, 1995;Kim, 2000) [42,51,18,43,48,54,20,33,13,14,53,9,25,26 ] and colon cancer ( [50,56,21] . Fortification of good fibre sources with meat increases the cooking yield due to its water-binding and fat-binding properties and to improve texture (Cofrades et al., 2000) [15] . ...
The aim of this work is to develop and investigate the shelf life of buffalo meat sausages fortified with foxtail millet (Setaria italica) at refrigerated storage temperature (0 °C). Studies on quality of sausage were done by analyzing different physico-chemical characteristics namely moisture content, ash content, pH, fat content, TBA number and microbial characteristic (total plate count and yeast & mould count) of the most appropriate combination of foxtail millet and meat, found with the help of Response Surface Methodology (RSM) software. The best combination as suggested by RSM was found to be 94.99 grams of meat mixed with 6.48 grams of foxtail millet. This was calculated so as to obtain the optimum range of moisture, ash, fat content and pH value. In total the four samples i.e. sausages prepared from whole meat, meat with foxtail millet, meat with foxtail millet plus sodium ascorbate and meat with foxtail millet plus tocopherol were taken for shelf life study. Sodium ascorbate (500ppm) and tocopherol (500ppm) were used as natural preservatives and hence the effect of such preservative on fortified sausages was also studied and was found that these assisted in improving the shelf life of the product. The product was acceptable for consumption even after 21 days of storage but total plate count, yeast and mould count and TBA number indicated the spoilage condition of sausage samples after 28 days. Therefore shelf life of the samples was found to be 21 days under refrigerated condition (0 °C). The study also provided evidences of increased dietary fibers and reduced fat content with high nutritional value in foxtail millet incorporated buffalo meat sausage, which can be considered as a functional food for healthy individuals and for patients of type 2 diabetes, cardiovascular diseases, obesity etc.
... Natural βcarotene dietary supplementation was found to inhibit LDL oxidation in patients with diabetes mellitus (Levy et al., 2000). Phenolic extracts containing caffeic acid and p-coumaric acid from rye were investigated against copper-catalyzed human LDL oxidation assay in vitro F I G U R E 3 Continued (Andreasen et al., 2001). This phenomenon may be influenced by the conjugation of carotenoids and LDL. ...
Antioxidant interaction among hydrophilic phytochemicals (caffeic acid, p‐coumaric acid) and lipophilic phytochemicals (β‐carotene, lycopene) in different mole ratios (n/n, 1:9, 3:7, 5:5, 7:3, 9:1) was evaluated. Assays performed were based on the scavenging activity of hydrogen peroxide (H2O2), the inhibition of low‐density lipoprotein oxidation (ox‐LDL) and DNA damage in vitro, using isobological analysis, synergistic rate (SR), and combination index (CI). Results showed that groups containing higher ratios of hydrophilic phytochemicals exhibited synergism while those containing higher ratios of lipophilic phytochemicals showed antagonism. Meanwhile, groups containing caffeic acid (e.g., caffeic acid:β‐carotene, 9:1) with more hydroxyl groups showed higher synergism (SR = 0.76 ± 0.02, CI = 0.77 ± 0.03) than groups containing p‐coumaric acid (e.g., p‐coumaric acid:β‐carotene, 9:1, SR = 0.88 ± 0.04, CI = 0.82 ± 0.05) on the scavenging activity of H2O2. Groups that contained lycopene (caffeic acid: lycopene, 9:1) with a higher ability of regeneration by phenolic acids showed more significant synergism (SR = 0.70 ± 0.02, CI = 0.79 ± 0.03) than groups containing β‐carotene (e.g., caffeic acid:β‐carotene, 9:1, SR = 1.00 ± 0.03, CI = 0.98 ± 0.04) on the inhibition of DNA damage. This study provided a basis for antioxidant interactions among phytochemicals against ox‐LDL and DNA damage in vivo. In addition, the choice of appropriate ratios and structures of hydrophilic and lipophilic phytochemicals should be considered in the diet and formulation of functional foods.
... 2.12.6.2. Hydroxybenzoic (C6-C1) and hydroxycinnamic acids (C6-C3) Hydroxycinnamic acids (Figure 2.22B) possess a higher antioxidant capacity compared to hydroxybenzoic acids (Figure 2.23A)(Andreasen et al., 2001). This difference might come from the -CH=CH-COOH group of hydroxycinnamic acids type because this group may give more remarkable H-donating ability and radical stabilization than the -COOH functional group case hydroxybenzoic acids(Rice-Evans et al., 1996). ...
apeseed and sunflower are the most cultivated oilseed plants in Europe in general, and in France in particular. Some industrialists are currently focusing on the development of industrial processes for the extraction/purification of proteins from the oil cakes of these two plants. These processes generate co-products which are saline aqueous effluents rich in phenolic compounds such as cholorgenic acid (CGA, for sunflower) and sinapine (SP, for rapeseed). The capture of these phenolic compounds, which can act as natural antioxidants and/or anti-inflammatory agents in nutrition and health, is therefore a promising way of valorization. The main objectives of this work were: 1) to characterize and identify the phenolic compounds of protein isolate by-products from SFM and RSM; 2) to select the best macroporous resins and to study the adsorption mechanism of phenolic compounds; 3) to optimize the conditions in the phenolic compounds adsorption column; and 4) to evaluate the biological activities of the obtained phenolic fractions, especially the antioxidant and anti-inflammatory properties.By different analytical methods, we determined that the liquid effluents consisted of phenolic compounds, amino acids, carbohydrates, and salt, which have a low molecular weight and can easily pass through a UF/DF membrane. All phenolic compounds were identified by HPLC and HPLC-ESI-MS analysis in comparison with standards. CGA is the main phenolic compound in the sunflower effluent. The main phenolic compound of rapeseed effluents is MS. Unlike sunflower, they also contain many other minor compounds. The adsorption/desorption of sunflower and rapeseed phenolic compounds was evaluated using different macroporous resins including XAD4, XAD7, XAD16, XAD1180 and HP20. We found that all phenolic compounds adsorbed readily onto the resins. XAD7 and XAD16 resins showed the best adsorption/desorption properties in sunflower and rapeseed liquid effluents, respectively. The results showed that the adsorption of all phenolic compounds follows a Langmuir model. According to the determined thermodynamic parameters, the adsorption process, is in all cases physical and is exothermic.The optimal condition for column adsorption was determined on the selected resins by experimental planning and multicriteria optimization. A multicriteria optimization methodology based on design of experiments showed the optimal conditions were adsorption flow rate of 15 BV/h at pH 2.7 for CGA from SFM. Meanwhile, adsorption flow rate of 13.3 BV/h and at pH ranging from 2 to 5 were the optimal conditions for sinapine from RSM. Ethanol solutions 50% (v/v) for chlorogenic acid, 70% (v/v) for sinapine were used for desorption.These approaches successfully produced the phenolic fractions for biological activities such as antioxidation and anti-inflammation. Phenolic fraction showed a higher antioxidant capacity than vitamin C in DPPH and ABTS assays (IC50/phenolic fractions < IC50 vitamin C, p < 0.05. In addition, it was discussed whether the phenolic fractions obtained in this project also showed an inflammatory effect. The sunflower fraction (CGA) effectively inhibited the production of TNF-α, which is a pro-inflammatory marker when a sample is treated with LPS. However, the rapeseed fractions were not effective against proinflammatory mediators. None of the fractions showed cytotoxicity.
... It is an important biological and structural component of the plant cell wall and it accumulates in soil and influences plant growth (Li et al., 2013;Paiva et al., 2013). FA is considered as non enzymatic antioxidant and acts under stress to elimi nate free radicals produced in plants (Andreasen et al., 2001;Engwa, 2018). Studies on the exogenous application of FA in plants have demonstrated that this compound acts as an important regulator of sev eral physiological processes related to plant growth and mitigating stress, such as, stomatal closure, cell division, membrane permeability, photosynthesis, respiration and many other metabolic processes (Santos et al., 2008;Li et al., 2013;Singh and Deen, 2014;Hussain et al., 2017;Cheng et al., 2018). ...
Salicylic acid (SA) and ferulic acid (FA) are considered phenolic compounds that act as elicitors due to their regulatory functions on plant growth, development, metabolic and physiological responses in plants. The aim of this research was to evaluate the effect of SA and FA on growth, fruit quality and synthesis of secondary metabolites in tomato (Solanum lycopersicum cultivar Santa Clara). The experiment was conducted in pots in a greenhouse. The application of SA and FA was performed at concentration of 1.0 mmol L-1 alone and in combination, with water treated plants as control. Exogenous application of SA and FA either alone or in combination (SA + FA) resulted in increases in biomass accumulation and chlorophyll contents in tomato plant; and soluble sugar, total polyphenol, flavonoids, lycopene and β-carotene contents in fruits. It was concluded that application of SA and FA resulted in higher production and concentration of secondary compounds in tomato.
... However, the study also observed that dimerization decreased the antioxidant potential of these phenolic derivatives. Andreasen, Landbo, Christensen, Hansen, and Meyer (2001) also investigated the antioxidative capacity of ferulic acid dehydrodimers from rye (whole grain, bran, and flour) on human low-density lipoproteins, and it was found that 8-O-4-diFA, the most abundant ferulic acid dehydrodimer (diFA) found in rye bran, showed better antioxidant action than ferulic acid. ...
Feruloylated arabinoxylan oligosaccharides (F-AXOS), commonly known as feruloylated oligosaccharides (FOs), are a group of functional oligosaccharides in which ferulic acid (FA) is esterified to l-arabinofuranosyl side chain of oligosaccharides. The main chain contains xylose backbone linked via β1-4 glycosidic bond, and arabinose residues are substituted on xylose with α1-3 and/or α1-2 glycosidic bond with 1%–3% of bound ferulic acid. These molecules own the nutritional properties of both FA and oligosaccharides. FOs are commonly extracted by chemical, physical or enzymatic methods. FOs from different sources carry various functional properties due to minute differences in their monosaccharide composition, presence of bound FA and its content, degree of polymerization, and arabinose substitutions. These are important bioactive natural molecules and have great potential in functional food development. The current chapter explores the occurrence, isolation, structures, potential health benefits, and functional food applications of FOs.
... Moreover, hydroxycinnamic acids (p-coumaric, ferulic and caffeic) were found, which constitutes another important group of antioxidant compounds. These substances present high antioxidant potential, with caffeic acid being the highest in antioxidant potential and p-coumaric acid the lowest in potential among the three (Andreasen et al. 2001). Dutra et al. (2017) observed similar phenolic acids' profile to that of this study in jocote and umbu (fruit and pulp), and reported higher levels of 2,5-dihydroxybenzoic (gentisic) and 3,4-dihydroxybenzoic (protocatechuic) acids. ...
The reuse of vegetable by-products has become one main global challenge. In this study, a central composite rotate design was used to obtain the optimal conditions (extraction time, ethanol concentration and extraction temperature) for the hydroethanolic extraction of bioactive compounds from Spondias mombin L. residue. The optimized extract (35 min, 70 °C and ethanol concentration of 55%) was analyzed for yellow flavonoids, tannins, ferric reducing antioxidant power (FRAP) as well as HPLC profile of phenolic compounds. This extract had 1666.18 ± 127.56 mg GAE 100 g−1 dm of total phenolic compounds, 38.03 ± 0.49 µg mL−1 of DPPH scavenging activity (IC50) and extraction yield of 17.44 ± 0.17%. The optimized extract showed strong FRAP antioxidant activity and high content of tannins and phenolic acids. Results indicated that 2,5-dihydroxybenzoic, salicylic, 4-hydroxybenzoic acid and ellagic acids were the main components in the optimized extract. High amounts of flavonoids were also noted, highlighting rutin, catechin and myricetin hydrates. The present results show that extracts from Spondias mombin L. agro-industrial waste would be helpful to design functional food products.
... Extracts of L. stenocephala contains phenolic substance represented by flavonoid [13,24]. S. cereale sprout also contains phenolic substance and it has been reported that antioxidant effects increase in proportion to the content of phenolic substance [14]. In the present study, TEES-10 ® consisted of chlorogenic acid, which is a dietary phenolic compound, and tricin, which is dietary flavonoids. ...
Complex extracts of Ligularia stenocephala Matsum. & Koidz. (LSE) and Secale cereale L. sprout (SCSE) (TEES-10®) were prepared. The purposes of the study were to evaluate anti-inflammatory activities of TEES-10® in vitro and to observe resolution of gingivitis in human with oral administration of TEES-10®. The effects of TEES-10® on normal periodontal ligament (PDL) cell viability, lipopolysaccharide (LPS) induced PDL cell viability and the changes of inflammatory mediator expression were evaluated in vitro. In the clinical trial, 150 mg of TEES-10® powder containing capsule was administered twice daily to the test group, while the control group administered placebos in a total 100 participants with gingivitis. Probing depth (PD), bleeding on probing (BOP), clinical attachment loss, gingival index (GI) and plaque index (PI) were measured at baseline and 4 weeks. Administering TEES-10® showed significant increase in PDL cell viability compared to administering LSE or SCSE alone. In addition, treating TEES-10® to LPS induced PDL cell significantly increased PDL cell viability compared to control. TEES-10® suppressed expression of NF-κB, p-ERK, ERK, COX-2, c-Fos and p-STAT and promoted expression of PPARγ in LPS induced PDL cells. In the clinical trial, significant improvement of GI and BOP was observed in the test group at 4 weeks. In addition, the number of patients diagnosed with gingivitis was significantly reduced in the test group at 4 weeks. Salivary MMP-8 and MMP-9 was also significantly decreased compared to placebo group. Within the limitations of this study, the TEES-10® would have an anti-inflammatory potential clinically in the chronic gingivitis patients.
... SA specifically inhibited NLRP3 inflammasome activation, but not priming. SA is one of the polyphenols that is abundantly present in the plant kingdom and can be obtained from diverse sources, such as cereals, fruit, and vegetables [43]. Polyphenols, the structure of which is composed of one or more benzene ring joined to hydroxyl groups, are the most abundant and safe antioxidant phytochemical compounds in the human diet. ...
A natural phenolic acid compound, sinapic acid (SA), is a cinnamic acid derivative that contains 3,5-dimethoxyl and 4-hydroxyl substitutions in the phenyl ring of cinnamic acid. SA is present in various orally edible natural herbs and cereals and is reported to have antioxidant, antitumor, anti-inflammatory, antibacterial, and neuroprotective activities. Although the anti-inflammatory function of SA has been reported, the effect of SA on the NOD-like receptor pyrin domain-containing 3 (NLRP3) inflammasome has not been explored. In the present study, to elucidate the anti-inflammatory mechanism of SA, we examined whether SA modulates the NLRP3 inflammasome. We found that SA blocked caspase-1 activation and IL-1β secretion by inhibiting NLRP3 inflammasome activation in bone marrow-derived macrophages (BMDMs). Apoptosis-associated speck-like protein containing CARD (ASC) pyroptosome formation was consistently blocked by SA treatment. SA specifically inhibited NLRP3 activation but not the NLRC4 or AIM2 inflammasomes. In addition, SA had no significant effect on the priming phase of the NLRP3 inflammasome, such as pro-IL-1β and NLRP3 inflammasome expression levels. Moreover, we found that SA attenuated IL-1β secretion in LPS-induced systemic inflammation in mice and reduced lethality from endotoxic shock. Our findings suggest that the natural compound SA has potential therapeutic value for the suppression of NLRP3 inflammasome-associated inflammatory diseases.
... It has been proven that hydroxycinnamic acids and their conjugates inhibit oxidative damage to the LDL. LDL oxidation protection by dietary antioxidants has been proven to inhibit coronary heart disease and atherosclerosis [68]. The presence of an aromatic ring in hydroxycinnamic acid derivatives plays a crucial role in their antioxidant activity. ...
... Rye grains have been scrutinized as a good source of fiber, and contain proteins, minerals and bioactive phenolic compounds that have been well documented for their health-benefiting effects [7][8][9][10][11]. Hundreds of bioactive phytochemicals from the extracts of natural resources have been identified and being studied for their health-benefiting antioxidant properties [10,[12][13][14]. Liu et al. [15] demonstrated that health-benefiting properties of food products are mainly due to the syringic and additive effects of bioactive compounds. ...
Six different solvents were used as extraction medium (water, methanol, ethanol, acidified methanol, benzene and acetone) to check their phenolics extraction efficacy from flour of two rye cultivars. Rye extracts with different solvents were further analyzed for the estimation of phytochemicals and antioxidant properties. Different tests (TPC, TAC, DPPH, FRAP, ABTS, RPA and CTC) were performed to check the antioxidant properties and tannin contents in extracts. A bioactive profile of a rye cultivar indicated the presence of total phenolic compounds (0.08–2.62 mg GAE/g), total antioxidant capacity (0.9–6.8 mg AAE/g) and condensed tannin content (4.24–9.28 mg CE/100 g). HPLC was done to check phenolics in rye extract with the best solvent (water), which indicated the presence of Catechol (91.1–120.4 mg/100 g), resorcinol (52–70.3 mg/100 g), vanillin (1.3–5.5 mg/100 g), ferulic acid (1.4–1.5 mg/100 g), quercetin (4.6–4.67 mg/100 g) and benzoic acid (5.3 mg/100 g) in rye extracts. The presence of DNA damage protection potential in rye extracts indicates its medicinal importance. Rye flour could be utilized in the preparation of antioxidant-rich health-benefiting food products.
... On the other hand, replacement of methoxyl chain at third and fifth position using -OH group under plasma exposure as reported in case of syringic acid increases the antioxidant activity. Through few works conducted in prior by Andreasen et al. (2001) it can be identified that hydroxycinnamic acids displays greater antioxidant activity related to equivalent hydroxybenzoic acids. This was owing to the fact that on exposure to plasma the acid groups present in hydroxycinnamic acid gets replaced with OH group which scavenges the free radical present and thus enhances the extract antioxidant activity. ...
Fruits and vegetables are the most important commodities of trade value among horticultural produce. They are utilized as raw or processed, owing to the presence of health-promoting components. Significant quantities of waste are produced during fruits and vegetables processing that are majorly accounted by waste peels (∼90–92%). These wastes, however, are usually exceptionally abundant in bioactive molecules. Retrieving these valuable compounds is a core objective for the valorization of waste peel, besides making them a prevailing source of beneficial additives in food and pharmaceutical industry. The current review is focused on extraction of bioactive compounds derived from fruit and vegetable waste peels and highlights the supreme attractive conventional and non-conventional extraction techniques, such as microwave-assisted, ultrasound assisted, pulsed electric fields, pulsed ohmic heating, pressurized liquid extraction, supercritical fluid extraction, pressurized hot water, high hydrostatic pressure, dielectric barrier discharge plasma extraction, enzyme-assisted extraction and the application of “green” solvents say as well as their synergistic effects that have been applied to recover bioactive from waste peels. Superior yields achieved with non-conventional technologies were identified to be of chief interest, considering direct positive economic consequences. This review also emphasizes leveraging efficient, modern extraction technologies for valorizing abundantly available low-cost waste peel, to achieve economical substitutes, whilst safeguarding the environment and building a circular economy. It is supposed that the findings discussed though this review might be a valuable tool for fruit and vegetable processing industry to imply an economical and effectual sustainable extraction methods, converting waste peel by-product to a high added value functional product.
... Ferulic acid as a component of olive seed powder [9] showed a potential inhibitory effect on LDL-C oxidation in vitro [60]. In the same line with the results of this study, Assini et al [61] reported that Naringrnin (one of the active components of olive seeds) is found to prevent the production of free fatty acids, hepatic steatosis, and VLDL-C in mice. ...
... WB is not only an excellent source of nutrients (13-18% protein, 3.5% fat, and 56% carbohydrates of which 70-90% is dietary fiber, DF) but also of bioactive components (tocopherols, phenolic compounds, carotenoids, etc.) [5][6][7][8][9][10] with recognized health benefits. Moreover, different authors have reported the important antioxidant activity of WB [7,9,11,12] and many studies have associated these properties to health benefits such as protection against low-density lipoprotein (LDL) oxidation system [13]. Additionally, it has been suggested that the antioxidant properties in WB may modulate cellular oxidative status and prevent biological oxidative damage, and that this consequently plays a role in reducing the risk of chronic diseases such as cardiovascular diseases (CVDs) and cancer [14]. ...
Wheat bran (WB) is a byproduct from the milling industry that contains bioactive compounds beneficial to human health. The aim of this work was on the one hand, increasing extracta-bility of antioxidant and anti-inflammatory compounds (specifically ferulic acid, FA), through en-zymatic hydrolysis combined with hydrothermal treatment (HT) and high hydrostatic pressure (HHP). On the other hand, enhancing the stability of final ingredient applying spray-drying (SPD) and microencapsulation (MEC). The use of HT increased FA, total phenolics (TP), and antioxidant capacity (AC) in WB hydrolysates, regardless the HT duration. However, the HT tested (30 min, HT30) produced a loss in anti-inflammatory activity (AIA). The combination of HT (15 min, HT15) with HHP increased AIA of the WB. SPD enhanced the TP yield in WB with no significant effect of inlet temperature (up to 140 °C) on phenolic profile mainly composed of trans-FA and smaller amounts of cis-FA and apigenin diglucosides. SPD caused a temperature-dependent increase in AC (160 °C > 140 °C > 130 °C). SPD inlet temperatures affected total solids yield (from 22 to 36%), with the highest values at 140 °C. The use of HHP in combination with HT resulted in >2-fold increase in total solids yield.
... Over the years, dietary fiber has received much positive attention with regard to its potential as a pharmafood, due to its ability to reduce cholesterol (Andreasen, et al., 2001;Anderson et al., 2009;Cui, et al., 2011 &Ajila andPrasada Rao, 2013), diabetes and coronary heart disease, prevention and treatment of obesity (Davidson and McDdonald, 1998;Bingham et al., 2003;Mann andCummings, 2009 &Elleuch et al., 2011) and ease constipation (Telrandhe et al., 2012;Rodriguez et al., 2006& Hauner et al., 2012. Nowadays, research show that the ingestion of suitable quantities of food fiber produces many beneficial effects on the digestive tract, such as the regulation of the intestinal function, improvement of the tolerance to glucose in diabetics (Pins et al., 2002 &Ajila andPrasada, 2013) or prevention of chronic diseases as colon cancer (Mongeau, 2003) and anti-carcinogenic effects (Scharlau et al., 2009 &Ajila andPrasada, 2013). ...
... Хидроксициметните киселини поседуваат повисока антиоксидантна активност во споредба со хидроксибензоевите киселини [112]. Повисоката активност на хидроксициметните киселини би можела да се должи на присуството на -CH=CH-COOH групи, коишто обезбедуваат поголема можност за донирање на водородни јони и стабилизација на радикалите во споредба со -COOH групата кај хидроксибензоевите киселини. ...
Os resíduos sólidos na fabricação de cerveja são gerados, principalmente na etapa de filtração do mosto, sendo constituídos de restos de casca e polpa dos grãos, misturados, em suspensão ou dissolvidos no mosto. Uma vez que a maior parte dos compostos fenólicos dos grãos de cevada estão contidos na casca, considera-se então que o resíduo ou bagaço de malte seja uma fonte potencialmente valiosa de compostos fenólicos. Estes conferem propriedades antioxidantes importantes para o organismo, prevenindo algumas patologias, que envolvem a participação dos radicais livres. Neste trabalho foi avaliado o teor de compostos fenólicos do bagaço de malte por espectrometria no ultravioleta/visível bem como a caracterização destes compostos por cromatografia liquida de alta eficiência (CLAE). O teor de fenóis totais neste extrato foi de 1,06 ± 0,54 mg EAG/g e 0,24 ± 0,07 mg EQ/g para flavonoides. A análise por CLAE revelou a presença do ácido gálico (2,43 ± 0,04 mg/g de extrato) e ácido p-cumárico (0,16 ± 0,01 mg/g de extrato), compostos antioxidantes conhecidos. A atividade antioxidante foi de CE50: 23,17 mg/mL, que indica a presença dos constituintes capazes de capturar os radicais livres como indicado pela análise por CLAE, caracterizando estes subprodutos como potencial fonte de compostos bioativos.
Cereal rye (Secale cereale) is a multi‐purpose crop, harvested for grain (for food, feed, and other products) as well as used as a forage or cover crop. The functionality of rye across these spheres is due to its abiotic and biotic stress tolerance and unique phytochemical composition. In this review, we focus on the current state and prospects of breeding rye for quality traits, where we define quality traits as grain, feed, or forage quality. Rye grain for human consumption has numerous healthful compounds, notably high dietary fiber content in grain and unique flavors that contribute to the signature properties of rye baked products and distilled spirits. As a forage, rye is useful in marginal environments and has high quality, including high crude protein, and is thus valuable for livestock production. While yield remains a major focus of breeding efforts, due to recent improvements in rye genomic and phenotypic resources, there are now opportunities for increased attention on breeding high‐quality ryes for multiple end uses. Through genetic improvement of quality traits, cereal rye has the potential to expand and serve multiple markets as a climate‐resilient crop.
As a result of increased interest in the production of plant-based drugs for the treatment of many diseases has become a significant reason why people have become more coversant in the use of traditional medicine for the treatment of mild and serious illness. Due to increase in the thrust for the production of plant-based drugs, this present study was carried out to compare the phytochemical constituents and antioxidant potencies of acetone, methanol and aqueous leaf extracts of Acalypha wilkesiana collected from Kaura Namoda Botanical Garden in Zamfara State-Nigeria. The antioxidant activities was evaluated using various assays; The total phenolic content of aqueous, methanol and acetone leaf extract were 15.58 0.66 mg GAE/g, 14.10 2.17 mg GAE/g and 8.70 0.01 mg GAE/g respectively. Total flavonol contents; 207.10 11.53 mg QE/g, 196.08 5.53 mg QE/g and 112.04 8.27 mg QE/g respectively. Total flavonoid contents; 240.99 9.50 mg QE/g, 252.52 3.73 mg QE/g and 123.88 5.58 mg QE/g respectively. FRAP values were 679.14 0.45 mmol/g, 611.90 7.09 mmol/g and 292.07 11.38mmol/g respectively. ABTS activity of aqueous, methanol and acetone leaf extract were 24.30 5.86 mg AAE/g, 14.49 1.02 mg AAE/g and 7.00 0.57 mg AAE/g respectively, methanol leaf extract had the highest percentage DPPH Inhibition value of 42.64 5.13, followed by aqueous (31.77 4.08) at 0.25mg/ml while aqueous had the highest (52.63 0.67), followed by methanol extract (44.80 2.80) at 0.50mg/ml. Aqueous extract had the highest percentage inhibition of Nitric Oxide with a value of 59.74 1.30, followed by methanol extract (46.11 2.54) at 0.25mg/ml. inhibition for aqueous was also highest at 0.5 mg/ml. Aqueous extract had the highest percentage lipid peroxidation inhibition value of 22.66 2.93, followed by methanol leaf extract with the value of 18.89 0.80 while at 0.50mg/ml methanol leaf extract had the highest percentage inhibition of lipid peroxidation (39.42 3.10), followed by aqueous leaf extract with the value of 31.48 1.61. The results showed that aqueous and methanol leaf extract of Acalypha wilkesiana displayed potent antioxidant effects with the aqueous having an edge. This present study therefore supports the view that Acalypha wilkesiana can be used in the management of oxidative stress and other related diseases.
The synthesis of a new class of 5’-arylchalcogenyl-3’-N-(E)-feruloyl-3’-amino-3’-deoxythymidine (AFAT) derivatives is disclosed. The compounds were obtained in good yields through an amidation reaction employing soft conditions. Both antitumoral activity against...
Gingivitis and periodontitis are inflammatory disorders caused by dental plaque and calculus. These disorders often lead to tooth loss if not treated properly. Although antibiotics can be used, it is hard to treat them due to the difficulty in supplying effective doses of antibiotics to lesion areas and side effects associated with long-term use of antibiotics. In the present study, attempts were made to provide in vitro and in vivo evidence to support anti-inflammatory activities of TEES-10®, a mixture of ethanol extracts of Ligularia stenocephala (LSE) and Secale cereale L. sprout (SCSE) toward gingivitis and periodontitis by performing the following experiments. TEES-10® with a ratio of 6:4 (LSE:SCSE) showed the best effects in both stimulating the viability and inhibiting the cytotoxicity. In in vitro experiments, TEES-10® showed an ability to scavenge 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals and remove ROS generated in periodontal ligament cells treated with lipopolysaccharide. TEES-10® also enhanced the viability of stem cells from human exfoliated deciduous teeth and stimulated the osteogenic differentiation of deciduous teeth cells. In in vivo experiments using rats with induced periodontitis, TEES-10® significantly decreased inflammatory cell infiltration and the numbers of osteoclasts, increased alveolar process volume and the numbers of osteoblasts, decreased serum levels of IL-1β and TNF-α (pro-inflammatory cytokines), and increased serum levels of IL-10 and IL-13 (anti-inflammatory cytokines). These results strongly support the theory that TEES-10® has the potential to be developed as a health functional food that can treat and prevent gingival and periodontal diseases and improve dental health.
Lipids a source of energy and can also be stored in body cells for proper cellular functions. Defects in lipid metabolism can lead to a wide range of metabolic disorders. A number of risk factors are generally responsible for the dysregulation of lipid metabolism and subsequently the development of metabolic diseases. In this chapter, the pathophysiology of several lipid-metabolism-related diseases has been discussed, and the therapeutic potential of different phytochemicals or plant-derived phytonutrients in managing these disorders are highlighted. There are several medicinal secondary metabolites, which could be highly significant to manage the lipid profile and prevent the development of serious outcomes of lipid-metabolism abnormalities such as hyperchylomicronemia, hypercholesterolemia, atherosclerosis, cancer, obesity, insulin sensitivity, and resistance. Many phytonutrients isolated from fruits, vegetables, and plant sources have presented their broad spectrum of medicinal activities to modulate metabolic processes and are also involved in lipid metabolism and the management of cholesterol levels in body. Bioactive compounds such as small molecular phytonutrients from natural sources have suggested prospective treatments against lipid-metabolism-related abnormalities and have been defined in this chapter. Considering diverse physiochemical properties and therapeutic value of phytonutrients, it is highly recommended to introduce more vegetables, and fruits in the dietary regimen to intake food containing fewer fats and high fibers so that it could significantly aid the management of lipid-metabolism-related diseases.
The elaboration of therapeutic protocols using natural compounds can help in improving the outcomes of many human conditions such as malignant disorders, neurodegenerative diseases, and systemic disorders. Recently, the attention of scientists was more focused on nutraceuticals as potential candidates that can be administered in the management strategy of various pathologies. This rise in nutraceutical applications is due to their relative safety and their pleiotropic effects. Several studies suggest the use of dietary regimens and food-derived substances for the prevention and treatment of many metabolic disorders that affect the central nervous system. The neuroprotective actions offered by these substances are mediated by their pertinent antiapoptotic, antiinflammatory, and antioxidative potentials. Some compounds may also intervene in the promotion of individuals’ health via the regulation of the process of autophagy and via the enhancement of the functionality of intracellular organelles such as mitochondria. Furthermore, healthy diet and the use of dietary supplements can directly influence the functions and the progeny of neural stem cells and the metabolism of microglial cells and can influence the polarization of macrophages in the nervous tissue resulting in better outcomes in some pathologic situations. In this chapter, we review the different roles and applications of nutraceuticals in the treatment of the major brain disorders that can affect human beings.
Metabolic diseases are devastating abnormalities that address human lives toward death if they are not correctly managed. Obesity and diabetes mellitus are the prime factors that induce insulin resistance to signaling pathways and increase the risk of cardiovascular diseases. Phytonutrients are the biologically active agents derived from natural sources such as vegetables, fruits, grains, cereals, and medicinal plants, and present the ability to boost the immune system of patients with metabolic disease and also enhance the conditions by the management of lipid profiles, insulin resistance and glucose homeostasis, and chemopreventive events in case of cancer disease. This chapter highlights some phytonutrients that may have issues with the gene and produce healthy and unhealthy interactions. However, the interaction between genetic and environmental factors such as intake of particular healthy and sufficient diet plans with a good lifestyle encourages the development and pathogenesis of diseases of polygenic dietary components. Phytonutrients are critical tools for the modulation of gene expressions involved in signaling pathways and phenotypes linked with metabolic diseases. It is also noted that human health is also affected by dietary nutrients having carcinogens and aflatoxin attached with them and influence the genetic variants. As the knowledge of carcinogen and anticarcinogen increases, nutritional science leads to promising therapeutics for cancer management by healthy diet plans. This chapter has depicted essential aspects of phytonutrients and their interactions with genes in metabolic disease prevention and treatments.
In spite of the advanced researches, preventive measures, and treatment options, cancer remains a growing ailment all over the world and its prevalence is estimated to increase in future. Cellular metabolic alterations have been documented as a hallmark of cancer. Metabolic regulation is an intricately coupled process whose deregulation leads to tumor progression as well as metastasis. In order to thrive in the living system, cancer cells adapt different metabolic pathways (bioenergetics and biosynthesis). They replenish their metabolic demands by switching from normal metabolism to cancer metabolism by the process of metabolic rewiring. Recent researches suggest that starving cancer cells by the use of nontoxic chemical entities can give promising results regarding cancer proliferation. Natural products, especially those of plant origin, offer different chemical scaffolds to target cancer via modulation of multiple cell signaling cascades. Phytonutrients, the secondary metabolites from the plants, constitute edible phytochemicals which are abundantly found in vegetables, whole grains, and fruits. The growing numbers of evidences suggest that phytonutrients exhibit anticancer as well as chemopreventive activities of these bioactive molecules against several cancers by targeting the various significant enzymes of glycolysis, the PPP pathway, TCA cycle, and serine metabolism. This book chapter presents an update for the scientific community about targeting the cancer metabolism by phytonutrients. The alterations in the cancer metabolism in the context of bioenergetics, biosynthesis, and mitochondrial functions have been discussed while presenting the impact of phytonutrients as modulators of potential metabolic effectors in the cancer metabolism.
Mitochondria are the main organelles responsible for generating cellular energy. The common symptom of mitochondrial disorders is extreme fatigue. The lowered mitochondrial activity owing to lack of chemical transmembrane capacity, changes in the electron transport chain’s function, the maintenance of the inner mitochondrial membrane’s electrical and decrease in essential metabolites transport to the mitochondria. The change in mitochondrial activity is brought about by the reduction of adenosine-5′-triphosphate (ATP) and oxidative phosphorylation. The mitochondrial activity needs regular replacement of natural phytochemicals and supplementations that help to maintain the energy level. The efficacy of oral alternative nutrients like reduced nicotinamide adenine dinucleotide (NADH), alpha-lipoic acid, coenzyme Q10, alpha-lipoic acid carnitine, membrane phospholipids, and other supplements was evaluated in clinical studies and were found effective against mitochondrial disorders. Combinations of these supplements can substantially alleviate weakness and other symptoms associated with mitochondrial disorders in patients. The frequent intake of these nutrients can also help to reduce the onset of various neurological disorders along with mitochondrial dysfunction. These results have significant effects on the welfare of both the civilian and military communities.
This study aimed to prepare and characterize chicken nugget formulations added with two agroindustrial byproducts, okara flour (OF) and rice bran (RB), as substitutes for chicken skin. The control formulation (F1) contained 8 wt% chicken skin, which was replaced with OF (F2), RB (F3), or a mixture of OF and RB in equal proportions (F4). OF and RB contained similar amounts of dietary fiber (∼30 g 100 g⁻¹), but RB had the highest concentrations of lipids and antioxidant compounds and OF the highest content of proteins and polyunsaturated fatty acids (PUFAs). Addition of byproducts to chicken nugget formulations increased the contents of dietary fibers (100%), ashes (35%), and PUFAs (10%) while reducing the contents of lipids (35%), saturated fatty acids (10%), and cholesterol (40%). F4 had the highest phytosterol (0.24 g 100 g⁻¹) and tocopherol (0.19 g 100 g⁻¹) contents and a similar texture profile to F1. F4 had better sensory acceptance and higher purchase intention than F2 and F3, and the scores for appearance, juiciness and texture were similar between F1 and F4. OF and RB are promising fat replacers to improve the nutritional value and cooking properties of chicken nugget formulations, contributing to reducing lipid oxidation rates.
Plant extracts contain a varied range of chemicals such as terpenoids, phenolic compounds, alkaloids, glucosinolates, and various organic acids. These chemicals are responsible for their unique nature and perceived biological activity of plant extracts. Owing to the wide acclaimed biological activities of plant extracts, they have been used as natural ingredients and have received significant renewed interest recently. Several plant extracts have been used as commercial preservatives in food because of their green image. The current chapter discusses various chemicals present in plant extracts and emphasizes the structure activity relationship of these chemicals.
Introduction A rapidly growing body of data documents associations between disease of the brain and small molecules generated by gut-microbiota (GMB). While such metabolites can affect brain function through a variety of mechanisms, the most direct action would be on the central nervous system (CNS) itself.Objective Identify indolic and phenolic GMB-dependent small molecules that reach bioactive concentrations in primate CNS.Methods
We conducted a PubMed search for metabolomic studies of the primate CNS [brain tissue or cerebrospinal fluid (CSF)] and then selected for phenolic or indolic metabolites that (i) had been quantified, (ii) were GMB-dependent. For each chemical we then conducted a search for studies of bioactivity conducted in vitro in human cells of any kind or in CNS cells from the mouse or rat.Results36 metabolites of interests were identified in primate CNS through targeted metabolomics. Quantification was available for 31/36 and in vitro bioactivity for 23/36. The reported CNS range for 8 metabolites 2-(3-hydroxyphenyl)acetic acid, 2-(4-hydroxyphenyl)acetic acid, 3-(3-hydroxyphenyl)propanoic acid, (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid [caffeic acid], 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-acetamido-3-(1H-indol-3-yl)propanoic acid [N-acetyltryptophan], 1H-indol-3-yl hydrogen sulfate [indoxyl-3-sulfate] overlapped with a bioactive concentration. However, the number and quality of relevant studies of CNS neurochemistry as well as of bioactivity were highly limited. Structural isomers, multiple metabolites and potential confounders were inadequately considered.Conclusion
The potential direct bioactivity of GMB-derived indolic and phenolic molecules on primate CNS remains largely unknown. The field requires additional strategies to identify and prioritize screening of the most promising small molecules that enter the CNS.
Hyperglycemia and hyperlipidemia-arbitrated mitochondrial oxidative insult is key reason for cardiac dysfunction and cardiomyopathy. Sinapic acid (SA) is a hydroxycinnamic acid (a polyphenolic acid) present in multiple plants and possesses several pharmacological activities. In this study, we examined the cardio protective effects of SA on streptozotocin (STZ)-induced cardiac insults. STZ and both STZ induced diabetes and normal control rats were administered with 20 and 40 mg/kg SA for 12 weeks. STZ rats demonstrated hyperglycemia and hyperlipidemia. Additionally, STZ administered rats exhibited various histological changes in the cardiac muscles and significantly enhanced CK-MB and LDH. The significant enhancement of oxidative stress, inflammation, and apoptotic markers, and the capacity to curb oxidative stress was significantly abridged in the STZ induced diabetic heart. Chronic treatment with SA (20–40 mg/kg) ameliorated the increased level of glucose, lipid, and cardiac function markers and curtailed histological changes in the cardiac muscles. Chronic treatment also repressed inflammation, oxidative stress and apoptosis thereby and restoring antioxidant defenses in the myocardium of STZ induced diabetic rats. STZ induced cardiac dysfunction and cardiomyopathy by promoting inflammation and oxidative stress. Sinapic acid ameliorates cardiac dysfunction and cardiomyopathy via improvement of hyperglycemia, hyperlipidemia, inflammation, oxidative stress, and apoptosis. Thus, SA possesses possible therapeutic value for the prevention of diabetic cardiac dysfunction and cardiomyopathy via the NRF2/HO-1 and NF-κB pathways.
Rye (Secale cereale) is a rich source of macromolecules, especially starch, fiber, and proteins which encourages the researchers and industries to use it for various purposes including bakery products, beverages and edible films formulation. However, despite many nutritional and health benefiting properties, rye has not been explored up to its full potential. Interest of consumers in formulating foods with high fiber and phenolic compounds has generated our interest in compiling the detailed information on rye. The present review on rye grains summarizes the existing scientific data on rye macronutrients (starch, arabinoxylan, β-glucan, fructan and proteins) and their corresponding industrial importance. Detailed description in this review unfolds the potential of rye grains for human nutrition. This review provides comprehensive knowledge and fills the remaining gap between the previous and latest scientific findings. Comprehensive information on rye nutrients along with health benefits will help to open a new era for scientific world and industrial sectors.
Sinapic acid (SA) was reported to protect against inflammation in various types of diseases. However, the role of SA in rheumatoid arthritis remains unclear. This study was designed to investigate the role of SA on rheumatoid arthritis. Rheumatoid arthritis mouse model was established by collagen immunization [collagen-induced arthritis (CIA)]. Histological analysis of articular cartilage tissue was carried out by hematoxylin and eosin (H&E) staining. Serum concentrations of tumor necrosis factor alpha and interleukin 6 were determined through enzyme-linked immunosorbent assay (ELISA). Oxidative damage indexes such as superoxide dismutase activity, malondialdehyde detection, glutathione detection, and catalase were determined by biochemical analysis. The protein levels of related genes were determined using Western blot. In CIA model, SA treatment attenuated paw swelling and clinical score of arthritis, attenuated articular cartilage tissues edema and infiltration of inflammatory cells, suppressed inflammatory cytokines release, and attenuated oxidative damage indexes. Mechanically, SA suppressed immune responses through inhibiting the IκB kinase (IKKs). SA attenuates rheumatoid arthritis through reducing inflammation and oxidative stress by downregulating IKKs.
Antioxidants are used to prevent oxidative changes and flavor development in oils and fats. The aim of this study is to evaluate the antioxidant effect of adding thyme powder added on sunflower oil during frying at different temperature intervals (250 ± 1 ° C). Thyme powders were added to sunflower oil at ratio of 0.5%, 1% and 1.5%, and the frying period were estimated for 2 hours at 250 ± 1 ° C. The oil samples collected intervals were at 0.5, 1, 1.5, and 2 hours and the potatoes were fried in each time. The antioxidant activity of thyme powders was 93.05 %, estimated using DPPH root scanning methods. The values of acid, peroxide and, the saponification, and the fatty acid content were considered criteria for evaluating the effectiveness of thyme powder in improving the quality of sunflower oil during frying. Our results confirmed that the adding thyme powder to sunflower oil improved their chemical properties, leading to decrease the acid, peroxide, and saponification values, and unsaturated fatty acids increased. Examination of serum function of rats fed with fried potatoes in sunflower oil-added thyme powder decreased total cholesterol, low-density lipoprotein, and triglycerides, while high-density lipoprotein increased. Moreover the results confirmed that thyme powder reduces liver and kidney functions compared to the control sample. Therefore, adding thyme to sunflower oil retards oxidative decomposition and improves its quality as a natural antioxidant to prolong oil stability.
Background
Cereal, pulse and oilseed processing by-products, specifically the brans/hulls, are enriched sources of phenolic compounds with antioxidant properties, yet they are typically disregarded as low-value animal feed or waste. Potential health-promoting effects of by-product phenolics are limited by the poor bioaccessibility and bioavailability of their bound phenolic constituents. Accumulating studies have shown solid-state fermentation (SSF) as an efficient strategy to enhance the release of bound phenolics from agro-industrial residues, leading to possible newfound human health attributes and greater value.
Scope and approach
In this review, we thoroughly discuss recent research on the effects of SSF on the composition, antioxidant activity, bioaccessibility, bioavailability and potential health benefits of phenolics from selected low-value cereal, pulse and oilseed processing by-products. We supplement this discussion by summarizing current knowledge on the phenolic profiles and existing limitations of these by-products to determine untapped research areas for SSF application.
Key findings and conclusions
Existing research on the phenolic profiles of various cereal, pulse and oilseed processing by-products indicate the presence of a wide variety of phenolics, making them excellent candidates for value-added use. SSF has been found to effectively enhance the bioaccessible and bioavailable phenolic contents in several of these by-products, allowing for improved in vitro antioxidant activities. Currently, there is a lack of in vivo studies to validate findings in vitro. Investigating the physiological health benefits of SSF treated processing by-products, in relation to various chronic diseases, is essentially a novel area of research that can drive the transformation of low-value by-products into value-added functional food ingredients.
Background
Beer is the most widely consumed fermented beverage in the world. Due to its antioxidation properties and other prebiotic effects related to non-alcoholic components, moderate drinking of beer is conducive to health. Antioxidants in beer, including phenolic compounds, melanoidins, selenium, vitamins B6, B12, E and C, etc., can effectively participate in the prevention of oxidative stress and prevent DNA damage, lipid peroxidation, and intermediate oxidative free radicals from attacking cellular components.
Scope and approach
In this review the importance of endogenous antioxidants in beer are described in order to improve the flavor stability and antioxidant activities (AOX) of beer. This study emphasizes the importance of brewing process controls to improve AOX, starting with optimization of the wort preparation and fermentation process to ensure the optimum technologies are used.
Key findings and conclusions
The optimization of malting, mashing and fermentation processes can increase the contents of phenolic compounds, melanoidins, selenium and vitamins C and E and AOX of malt. Decoction mashing is more conducive to promoting the formation of phenolic compounds and melanoidins than infusion mashing. Rapid cooling following heat treatment and boiling can be used to increase the contents of melanoidins. The use of excellent yeast, an appropriate pitching rate, high gravity wort and low-temperature fermentation is more beneficial for the maintenance of high AOX in beer. It is effective to selectively add exogenous antioxidants rich in plant phenolic compounds or micronutrients to improve the AOX of beer.
The aim of the present work was to examine the effect of cross-linking of rye and wheat arabinoxylan by ferulic acid on grain nutritive value, measured in vitro by an enzymatic test. Determination of ferulic acid was based on spectrophotometric measurements of defatted samples at 320 nm. Approximately 80% of the trans-ferulic acid, the dominant phenolic acid of rye and wheat grain, was found in the bran of both species. Total content and extractability of free and esterified ferulic acid by water, ethanol, and alimentary enzymes (soluble dietary fiber) from grain meal were significantly higher in rye than in wheat. The activity of peroxidase, the enzyme thought to be responsible for the formation of diferulic bridges, was also significantly higher in rye. Most (85-90%) of the alkaline-soluble ferulic acid in grain was localized in the insoluble dietary fiber, and only about 5% was in the soluble fraction. In spite of the higher solubility of rye arabinoxylans and the higher arabinose-xylose ratio in rye than in wheat grain, the ratio of the number of arabinose residues per ferulic acid molecule was not significantly higher in the soluble fiber of rye. Thus, cross-linking of grain hemicellulose components by ferulic bridges does not appear to contribute to the known differences in the structure, molecular weight, and nutritive properties of soluble fiber of rye and wheat.
Ferulic acid (FA) is a low molecular weight phenolic acid that is a common component of the outer layers of cereal grains. It has been implicated in resistance to both insect and fungal pathogens. The FA concentrations of 18 cultivars of 2-row and 6-row barleys, grown in 2 locations, were quantified by HPLC analysis following acid hydrolysis. The FA concentrations ranged from 365 to 605 μg/g dry weight. The concentration of FA varied significantly among the different cultivars of barley. A genetic basis for FA levels is inferred by the similar ranking of the cultivars in both locations. FA levels were also measured by the absorbance at 340 nm of the acid-hydrolyzed extract, and in situ detection of fluorescence intensity of the ground grain using a UMSP80 microspectro-fluorimeter. Both of these methods are more rapid than HPLC and may allow the practical screening of FA concentrations in numerous barley lines.
Oxidative modification of low-density lipoprotein (LDL) is believed to play a crucial role in atherogenesis. The antioxidant activity of hydroxycinnamic acids typically present in fruits was investigated in vitro using a human LDL oxidation assay. The o-dihydroxy compounds caffeic, caftaric, chlorogenic, and neochlorogenic acids had highest antioxidant activities and inhibited LDL oxidation from 86 to 97% at 5 µM. Ferulic and fertaric acids had lower antioxidant activities, and p-coumaric and p-coutaric acids had the lowest. Differences in antioxidant activity were thus primarily related to the hydroxylation and methylation pattern. The esterification to tartaric acid slightly enhanced the antioxidant activity of p-coumaric and ferulic acids, but esterification of caffeic acid to quinic acid (as in chlorogenic and neochlorogenic acid) had no effect on or slightly decreased antioxidant activity. The observed differences in activities are discussed in terms of structural dissimilarities of the compounds. It is proposed that for the less active hydroxycinnamic acids, p-coumaric and ferulic acids, esterification to tartaric acid may enhance their ability to inhibit LDL oxidation by binding to apolipoprotein B in the LDL particle.
Seven isomeric dehydrodimers of ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been synthesized and identified in extracts of saponified cell walls of cocksfoot, switchgrass, and suspension-cultured corn. Dehydrodimers (E,E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′-bicinnamic acid, trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2, 3-dihydrobenzofuran-3-carboxylic acid, (Z)-β-{4-[(E)-2-carboxyvinyl]-2- methoxyphenoxy}-4-hydroxy-3-methoxycinnamic acid, (E)-3-{4-[(E)-2-carboxyvinyl]- 2-methoxyphenoxy}-4-hydroxy-5-methoxycinnamic acid, (E,E)-4,4′-dihydroxy- 3,5′-dimethoxy-β,3′-bicinnamic acid, 4,4′-dihydroxy-3, 3′-dimethoxy-β,β′-bicinnamic acid, and trans-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1,2-dihydronaphthalene- 2,3-dicarboxylic acid, all arise from oxidative coupling of ferulate esters in cell walls and represent products of 8-5, 8-8, 8-O-4, 4-O-5, and 5-5 radical coupling. Prior literature has acknowledged only the presence of the 5-5-coupled dehydrodimer (E,E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′- bicinnamic acid. Consequently, by measuring only a single dehydrodimer and assuming inappropriate response factors, ferulate dehydrodimers have been underestimated by factors of up to 20. Synthetic routes to all seven isomers have been developed to provide structural authentication and determination of GC response factors.
Dimers of ferulic acid were chemically synthesized and the antioxidant properties assessed using (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes and (b) scavenging of the radical cation of 2,2'-azinobis(3-ethyl-benzothiazoline-6-sulphonate (ABTS) relative to the water-soluble vitamin E analogue, Trolox C (expressed as Trolox C equivalent antioxidant capacity, TEAC). The dimers examined were (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid (5-5' diFA), trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2,3 -dihydrobenzofuran-3-carboxylic acid (5,8'-BenDiFA) and the methyl ester of 5,8'-BenDiFA, dimethyl-5,8'-BenDiFA. In both assays, the order of antioxidant efficacy was: 5,5'-diFA > 5,8'-BenDiFA > dimethyl-5,8'-BenDiFA. From these results, methyl esterification decreases the antioxidant action. Comparison of the TEAC values shows that 1 mol of each of the ferulic acid dimers tested is less effective than 2 mol of free ferulic acid, and so dimerization decreases antioxidant action of these hydroxycinnamates.
The interaction of four phenolic acids, representative of three chemical groups present in human diet, with peroxyl radicals was studied in vitro in a low density lipoprotein (LDL) oxidation model. The controlled oxidation of LDL was initiated by free radicals generated from a hydrophilic azo initiator and followed by monitoring the oxygen consumption and the fluorescence quenching of cis-parinaric acid previously incorporated into LDL. The hydroxycinnamic acid derivatives, chlorogenic and caffeic acids, have high stoichiometric numbers and reactivity with peroxyl radicals as compared with trolox, the water-soluble analogue of vitamin E, whereas ellagic acid (a tannic compound) compares with trolox effects. Protocatechuic acid (a hydroxybenzoic acid derivative) exhibits a complex reaction with peroxyl radicals, as indicated by UV spectroscopy, resulting in undefined inhibition periods of LDL oxidation and low reactivity with peroxyl radicals. Presumably, secondary radicals of these compounds are unable to initiate LDL oxidation. The antioxidant activity of the various phenolic compounds is discussed in terms of structure-activity relationships.
The dehydrodiferulic acid content of different common and durum wheat grains and milling fractions was determined by an HPLC procedure. The 8-O-4′, 5–8′ benzofuran, 5–8′ and 5-5′ dehydrodimers were identified in all samples studied and occurred in decreasing relative amounts, respectively. Durum wheats were twice as concentrated in dimers as common wheats. An important genetic variation for dehydrodiferulic acid content was shown within durum wheat grains, whereas the agronomic conditions had no effect. There was 10 to 20 times more dehydrodiferulic acids in external layers (aleurone, bran) than in the starchy endosperm of durum wheat grains. The content and composition in dimers of the inner endosperm did not vary according to genotypes and cultivation conditions. The ratio of dehydrodimers to monomers of ferulic acid which represented an index of dimerisation, was 1·6 times higher in the external layers of the grain than in the endosperm. No relation was found, however, between the degree of ferulic acid dimerisation and the milling behaviour of durum wheat grains.
Nineteen enzymatic activities of Maxilact 20.000 have been assayed using the API ZYM micromethod. Some of them have been found to be positive and these have been studied in more detail. Hydrolysis of lactulose by the action of β-galactosidase is slower than that of lactose. Proteolytic activity has been found in both the soluble and insoluble fractions of Maxilact. Optimum temperature and pH are 45°C and 7, respectively. The action of Maxilact on casein did not alter β-casein, but degraded αs-casein to give a peptide with electrophoretic mobility similar to that produced by the action of rennet. A weak lipolytic activity on tributyrine was also detected.
Feruloyl and p-coumaroyl groups in spinach cell walls (CW) were labelled using [14C]cinnamic acid and fed to rats. In the caecum and colon, ferulic acid (FA) and p-coumaric acid (PCA) were released from the CW. Few feruloyl or coumaroyl groups remained in the CW to be excreted in faeces, and thus the presence of simple phenol-sugar esters provided little protection of the polysaccharides to enzymic attack. Some oxidatively coupled phenols were also released but a portion remained in the CW. The oxidatively coupled phenols accumulated in the gut whereas the FA and PCA were absorbed by the rat. Thus enzyme-resistant fragments, containing oxidatively coupled phenols (and possibly sugar residues), may survive microbial attack by rat intestinal bacteria.
8-8-Diferulic acid (non-cyclic form) (4,4′-dihydroxy-3,3′-dimethoxy-β,β′-bicinnamic acid) was chemically synthesised and the antioxidant properties were assessed using (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes, and (b) scavenging of the radical cation of ABTS (2,2′-azinobis (3-ethyl-benzothiazoline-6-sulphonate)) relative to the water-soluble vitamin E analogue, Trolox C. The structure of the chemically synthesised 8-8 dimer was confirmed by 1H-NMR and mass spectrometry. Its absorption properties in ethanol were: λmax1: 320 nm; λmax2: 287 nm; λmin: 256 nm; ελmax1 (M−1 cm−1): 14 200±1700 and ελmax2 (M−1 cm−1): 14 300±1300. The 8-8 dimer showed the best antioxidant properties in the aqueous phase assay among the esterified dimers present in plant cell walls. Like the other ferulic dimers, 8-8-diferulic acid is a better inhibitor of lipid peroxidation than ferulic acid on a molar basis. Some of the factors possibly involved in the antioxidant effect of these compounds are: number of free hydroxyl groups in the molecule, stability of transient radical and partition coefficient.© 1999 Society of Chemical Industry
It has been shown that a common side-chain of grass cell wall arabinoxylans is 2-O-β-D-xylopyranosyl-(5-O-feruloyl)-L-arabinose [X(F)A]. The stability of X(F)A was determined by incubation of (feruloyl-U-14C)-labelled X(F)A and (pentosyl-1-3H)-labelled X(F)A anaerobically with rat caecal contents and chromatographic analysis of the radioactive products. The ester linkage was hydrolysed very rapidly to form ferulic acid (which was stable) and the disaccharide (XA). The 3H-XA was further metabolised, but 3H-monosaccharides did not accumulate. In the end-products of fermentation of (pentosyl-3H)-labelled X(F)A, 67% of the 3H was present in bacterial polymers. In contrast, when free [1-3H]arabinose was incubated with rat caecal contents, 74% of the 3H quickly became volatile, probably as 3H2O. It is concluded that X(F)A is highly susceptible to (feruloyl)esterase activity produced by bacteria present in the rat caecum, and that the disaccharide produced is further fermented, but not via the production of extracellular arabinose and xylose. © 1997 SCI.
Seven isomeric dehydrodimers of ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been synthesized and identified in extracts of saponified cell walls of cocksfoot, switchgrass, and suspension-cultured corn. Dehydrodimers (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid, trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid, (Z)-beta-{4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy}-4-hydroxy-3-methoxy-cinnamic acid, (E)-3-{4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy}-4-hydroxy-5-methoxycinnamic acid. (E,E)-4,4'-dihydroxy-3,5'-dimethoxy-beta,3'-bicinnamic acid, 4,4'-dihydroxy-3,3'-dimethoxy-beta,beta'-bicinnamic acid, and trans-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid, all arise from oxidative coupling of ferulate esters in cell walls and represent products of 8-5, 8-8, 8-O-4, 4-O-5, and 5-5 radical coupling. Prior literature has acknowledged only the presence of the 5-5-coupled dehydrodimer (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid. Consequently, by measuring only a single dehydrodimer and assuming inappropriate response factors, ferulate dehydrodimers have been underestimated by factors of up to 20. Synthetic routes to all seven isomers have been developed to provide structural authentication and determination of GC response factors.
Oxidative modification of low-density lipoprotein (LDL) is believed to play a crucial role in atherogenesis. The antioxidant activity of hydroxycinnamic acids typically present in fruits was investigated in vitro using a human LDL oxidation assay. The o-dihydroxy compounds caffeic, caftaric, chlorogenic, and neochlorogenic acids had highest antioxidant activities and inhibited LDL oxidation from 86 to 97% at 5 μM. Ferulic and fertaric acids had lower antioxidant activities, and p-coumaric and p-coutaric acids had the lowest. Differences in antioxidant activity were thus primarily related to the hydroxylation and methylation pattern. The esterification to tartaric acid slightly enhanced the antioxidant activity of p-coumaric and ferulic acids, but esterification of caffeic acid to quinic acid (as in chlorogenic and neochlorogenic acid) had no effect on or slightly decreased antioxidant activity. The observed differences in activities are discussed in terms of structural dissimilarities of the compounds. It is proposed that for the less active hydroxycinnamic acids, p-coumaric and ferulic acids, esterification to tartaric acid may enhance their ability to inhibit LDL oxidation by binding to apolipoprotein B in the LDL particle. Keywords: Antioxidant; LDL; p-coumaric, ferulic, caffeic, hydroxycinnamoyltartaric acids; hydroxycinnamoylquinic acids
The antioxidant activity of feruloyl arabinose, a model substance of cereal cell-wall fragments, in the LDL autoxidation system by CuSO4 and its absorption were studied. Ferulic acid added as free acid showed little suppressive effect on LDL oxidation. However, ferulic acid sugar esters showed a positive effect. This fact indicated that affinity of LDL particle and free or bound ferulic acid is important for the suppressive effect. The HPLC analysis showed that in rats administered feruloyl arabinose, two peaks were detected with retention times lower than those of feruloyl arabinose and ferulic acid, which appeared upon β-glucuronidase/sulfatase treatment. The study showed that the absorbed form of FAA could be a more polar compound, possibly a conjugated form. Keywords: Antioxidant; low-density lipoprotein; cereal cell wall; ferulic acid sugar ester
The action of wheat bran as a potential colon anticarcinogen is related partly to its low fermentability in the large intestine. Phenolic acids are highly bioactive components and also limit degradability of wheat bran in ruminants. Therefore, the solubilization of covalently bound phenolic acids during the fermentation of wheat bran in a human model colon was examined. Phenolics were only partially and relatively slowly solubilized from wheat bran, but were rapidly and fully solubilized from sugarbeet fiber; the levels of free ferulic acid in fermentation liquors remained very low and did not reflect the amounts solubilized from fiber sources. Xylanase and ferulic acid esterase activities were shown to be present. The released ferulic acid did not appear to bind noncovalently to the residual wheat bran fiber. Thus, fermentation in the gut alters the partition of esterified phenolic acids from the insoluble residue and the soluble fraction, where microbial ferulic acid esterase(s) can potentially yield free ferulic acid. Keywords: Ferulic acid; phenolic acids; plant cell walls; fiber; wheat bran; sugarbeet pulp; colon fermentation; phenolic antioxidants; esterases; xylanase
Feruloyl and p-coumaroyl groups in spinach cell walls (CW) were labelled using [14C]cinnamic acid and fed to rats. In the caecum and colon, ferulic acid (FA) and p-coumaric acid (PCA) were released from the CW. Few feruloyl or coumaroyl groups remained in the CW to be excreted in faeces, and thus the presence of simple phenol–sugar esters provided little protection of the polysaccharides to enzymic attack. Some oxidatively coupled phenols were also released but a portion remained in the CW. The oxidatively coupled phenols accumulated in the gut whereas the FA and PCA were absorbed by the rat. Thus enzyme-resistant fragments, containing oxidatively coupled phenols (and possibly sugar residues), may survive microbial attack by rat intestinal bacteria.
An optimized high performance liquid chromatography (HPLC) procedure has been developed for the analysis and quantification of all of the known ferulic acid dehydrodimers, and the principle phenolic aldehydes and acids, found in the cell walls of higher plants. The HPLC system uses an ODS2 reverse phase column (5 μm particle size) eluted with a methanol, acetonitrile and water gradient with detection at 280 nm. In addition to providing baseline resolution of most components, the method employs a spectrometric detector which enables the precise identification of eluted components through the analysis of their spectral properties. Analysis of the cell wall phenolics of wheat straw stem (Triticum vulgare) was carried out using this method which is highly versatile and, for certain components, more sensitive than the current gas chromatography–mass spectrometry methodology.
Four ferulic acid dehydrodimers were isolated from rye bran and purified by preparative HPLC after alkaline hydrolysis. The identity of the compounds were confirmed by UV,1H and13C-NMR and mass spectroscopy. The content of the four identified dimers corresponded to a total dimer concentration of 307 μg/g (dry matter) of the whole grain. The concentrations in the bran fraction were 10–20 times higher than in the starchy endosperm. The four dimers were in decreasing amounts: ((Z)- β -{4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy}-4-hydroxy-3-methoxy-cinnamic acid (8-O-4′-DiFA);trans -5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (8-5′-DiFA benzofuran form), (E,E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′-bicinnamic acid (5-5′-DiFA) and (E,E)-4,4′-dihydroxy-3,5′-dimethoxy-β,3′-bicinnamic acid (8-5′-DiFA). The ferulic acid dehydrodimers were also synthesised by a simple procedure from ethyl ferulate using peroxidase and hydrogen peroxide.
The antioxidant properties of a series of polyhydroxy flavonoids and related compounds have been evaluated. The results have been correlated with the structures of the compounds concerned, which hale been shown to Junction mainly as primary antioxidants. The ability of some such compounds to form complexes with copper has been demonstrated from a study of UV spectra and is probably a contributing factor to the stabilising effects of such compounds.Antioxidant activity is favoured by a multiplicity of phenolic hydroxyl groups and depends critically on the co-operation of the 4-carbonyl with either the 3- or the 5-hydroxyl groups. Dihydro-flavones are slightly more active than the corresponding flavones.
Cell wall polysaccharides contain a small amount of ester-linked hydroxycinnamic acid derivatives, such as p-coumaric and ferulic acids. These hydroxycinnamic acids can be coupled oxidatively to form the acid dimers. Dimer formation in the growing plant cell wall would cause the cross-linkage of cell wall polysaccharides and lead to an increase in wall rigidity. Feruloyl polysaccharide esters would also participate with lignin monomers in oxidative coupling pathways to generate a ferulate-polysaccharide-lignin complexes during cell wall development. Feruloyl oligosaccharides derived from feruloyl polysaccharides have been shown to inhibit cell elongation growth induced by auxin or gibberellins. Feruloyl polysaccharides are critical entities in directing wall cross-linking and in limiting biodegradability by microorganisms.
The purpose of this study is to provide a comprehensive survey on the compositional properties of LDL (e.g., lipid classes, fatty acids, antioxidants) relevant for its susceptibility to oxidation, on the mechanism and kinetics of LDL oxidation, and on the chemical and physico-chemical properties of LDL oxidized by exposure to copper ions. Studies on the occurrence of oxidized LDL in plasma, arteries, and plaques of humans and experimental animals are discussed with particular focus on the use of poly- and monoclonal antibodies for immunochemical demonstration of apolipoprotein B modifications characteristic for lipid peroxidation. Apart from uptake of oxidized LDL by macrophages, studies describing biological effects of heavily or minimally oxidized LDL are only briefly addressed, since several reviews dealing with this subject were recently published. This article is concluded with a section on the role of natural and synthetic antioxidants in protecting LDL against oxidation, as well as some previously unpublished material from our laboratories.
Total arabinoxylan (AXt), water-extractable arabinoxylan (WeAX) and ferulic acid (FA) from five cultivars of durum wheat (Triticum durumL.), grown under four different agronomic conditions, were measured. Among the varieties analysed, AXt, WeAX and FA contents ranged between 4·07%–6·02%, 0·37%–0·56% and 0·784 mg/g–7·98 mg/g, respectively. High genetic and agronomic variability was detected for AXt, WeAX and FA. AXt and FA increased sharply in milling products for extraction rates above 60%. FA was quantified in durum wheat milling fractions. High concentrations of FA esterified to cell-wall arabinoxylans were found in the aleurone layer (69% of total FA), germ and seedcoat (26·6% of total FA). Only trace amounts were detected in the starchy endosperm (1·4% of total FA). A highly significant correlation appeared between AXt and FA contents.
Ferulate polysaccharide esters in grasses enter into free-radical condensation reactions in the cell wall. By radical dimerisation of ferulates, polysaccharide-polysaccharide cross-linking is effected. A range of diferulate isomers are produced, not solely the 5-5' -coupled dimer which has been quantified historically. Both ferulates and diferulates enter lignification reactions and become intimately bound up with the lignin complex. Again, under-quantification is significant since it is not possible to release ferulate or diferulates from some of the structures. Overall, ferulates play a significant role in cell wall development and impact polysaccharide utilisation in grasses.
Ferulic acid is a ubiquitous plant constituent that arises from the metabolism of phenylalanine and tyrosine. It occurs primarily in seeds and leaves both in its free form and covalently linked to lignin and other biopolymers. Due to its phenolic nucleus and an extended side chain conjugation, it readily forms a resonance stabilized phenoxy radical which accounts for its potent antioxidant potential. UV absorption by ferulic acid catalyzes stable phenoxy radical formation and thereby potentiates its ability to terminate free radical chain reactions. By virtue of effectively scavenging deleterious radicals and suppressing radiation-induced oxidative reactions, ferulic acid may serve an important antioxidant function in preserving physiological integrity of cells exposed to both air and impinging UV radiation. Similar photoprotection is afforded to skin by ferulic acid dissolved in cosmetic lotions. Its addition to foods inhibits lipid peroxidation and subsequent oxidative spoilage. By the same mechanism ferulic acid may protect against various inflammatory diseases. A number of other industrial applications are based on the antioxidant potential of ferulic acid.
The kinetics of the oxidation of human low density lipoprotein (LDL) can be measured continuously by monitoring the change of the 234 nm diene absorption. The time-course shows three consecutive phases, a lag-phase during which the diene absorption increases only weakly, a propagation phase with a rapid increase of the diene absorption and finally a decomposition phase. The increase of the dienes is highly correlated with the increase of MDA or lipid hydroperoxides. The duration of the lag-phase is determined by the endogenous antioxidants contained in LDL (vitamin E, carotenoids, retinylstearate). Water-soluble antioxidants (ascorbic acid, urate) added in micromolar concentrations prolong the lag-phase in a concentration-dependent manner. The determination of the lag-phase is a convenient and objective procedure for determining the susceptibility of LDL from different donors towards oxidation as well as effects of pro- and antioxidants.
The decrease of the tryptophan fluorescence (Ex/Em = 282/331 nm) was used to monitor the kinetics of copper-mediated LDL oxidation. Cu2+ causes a concentration-dependent quenching of the LDL Trp-fluorescence, the maximum of about 22% suggests that 8-9 Trp residues (out of a total of 37) are accessible for Cu2+ ions. Decomposition of LDL tryptophan commences immediately after addition of Cu2+ and proceeds in two stages with quite different rates. At a molar ratio of Cu2+/LDL = 33:1 the LDL particle looses 1 Trp every 13.5 min in the initial slow phase and every 4.1 min in the subsequent rapid The second, stage temporarily coincides with the propagating lipid peroxidation. In the initial phase loss of Trp proceeds with a constant rate for up to 200 min depending on the copper concentration. Whereas lipid peroxidation accelerates after consumption of vitamin E, rate of Trp loss does not increase. Loading of LDL with vitamin E has also no effect on the initial rate of Trp loss. During the initial phase a loss of one Trp residue/LDL is accompanied by the loss of two alpha-tocopherols and the generation of two conjugated lipid hydroperoxides. The results suggest Trp residues play a role in initiating the lipid peroxidation process in the LDL particle. In such kinetic studies, precautions must be taken to avoid photodecomposition of LDL-Trp. The LDL vitamin E fluorescence (Ex/Em = 290/323 nm) does not interfere with the Trp fluorescence even at high concentrations.
Atherosclerosis, the principal cause of heart attack, stroke and gangrene of the extremities, is responsible for 50% of all mortality in the USA, Europe and Japan. The lesions result from an excessive, inflammatory-fibroproliferative response to various forms of insult to the endothelium and smooth muscle of the artery wall. A large number of growth factors, cytokines and vasoregulatory molecules participate in this process. Our ability to control the expression of genes encoding these molecules and to target specific cell types provides opportunities to develop new diagnostic and therapeutic agents to induce the regression of the lesions and, possibly, to prevent their formation.
The antioxidant activity of the major phenols derived from hydroxycinnamic acid (caffeic, ferulic, and p-coumaric acids) on in vitro LDL oxidation was screened, using Cu2+ as catalyst. The presence of the second phenolic hydroxy group enhanced the inhibitory effect of these compounds. In fact, at 5 microM concentration, only caffeic acid completely protected LDL from modification as measured as conjugated dienes formation and apo B-100 fragmentation, also preserving alpha-tocopherol. The effect of caffeic acid in inhibiting LDL oxidative modification induced by three different oxidant systems was tested. Using both Cu2+ and 2,2'-azobis (2-amidinopropane)-hydrochloride (AAPH), the inhibitory effect of caffeic acid was dose-dependent. Yet, the better protection was achieved in the metal-ion dependent system. Also the murine macrophages-mediated LDL oxidation was efficiently inhibited by 5 microM caffeic acid. UV-VIS spectra of caffeic acid incubated with cupric ions show the formation of a caffeic acid:copper complex, responsible for a transient chelating activity. This mechanism, coupled with its free radical scavenging property, accounts for the higher inhibitory activity exhibited by caffeic in Cu(2+)-catalyzed reaction.
Dietary guidance recommends consumption of whole grains to reduce the risk of chronic diseases including cancer and cardiovascular disease. Epidemiologic studies support the belief that whole grains are protective against cancers, especially gastrointestinal cancers such as gastric and colonic, and cardiovascular disease. Components in whole grains that may be protective are diverse and include compounds that affect the gut environment, i.e., dietary fiber, resistant starch, and other undigestible compounds in whole grains, compounds that function as antioxidants such as trace minerals and phenolic compounds, and compounds that are phytoestrogens with potential hormonal effects. Many of the protective compounds in whole grains are also in fruits and vegetables, but some plant compounds are more concentrated in whole grains, such as phenolic compounds including ferulic and caffeic acid. Other potential mechanistic effects of whole grains include binding of carcinogens and modulation of glycemic index. Clearly, the range of protective substances in whole grains is impressive, and advice to consume additional whole grains is justifiable.
1. An antioxidant effect of phenolic substances in red wine to reduce oxidizability of low-density lipoprotein has been proposed as the basis for a relatively lower incidence of coronary disease in populations with high red wine intake. We have now investigated the possible antioxidant effects of various beverages, including red wines, white wines, beers and red grape juices (diluted 1:500), on metal ion-dependent (copper) and -independent (aqueous peroxyl radicals) oxidation of isolated human low-density lipoprotein. We also tested the effects of these beverages on copper-initiated oxidation of lipoproteins in serum.
2. The higher the polyphenolic content of a beverage, the greater was its antioxidative effect measured as change in lag time in the different oxidation systems. Upon stripping the polyphenolics from the drinks, the lag times returned to control levels in isolated low-density lipoprotein; however, the low concentrations of phenolics remaining after stripping had a lesser but still significant effect on oxidation of lipoproteins in serum. The inhibitory effect of these phenolics appeared to be more pronounced for metal ion (copper)-induced oxidation than for those induced by aqueous peroxyl radicals, suggesting that both copper-binding and free radical-trapping activities may be involved. A mixture of the carboxylic acids representative of those present in red wine exhibited no significant effect on lag time of metal iondependent and -independent low-density lipoprotein oxidations. Ethanol, at concentrations of 0.1–0.5%, had no effect on either copper-induced or aqueous peroxyl radical oxidations.
3. Extracts of acid-hydrolysed red wine were separated by thin-layer chromatography and the most active antioxidant fractions identified. GC-MS and HPLC analysis of these fractions resulted in the identification of several cinnamic acid derivatives, such as coumaric acid, caffeic acid and protocatechuic acid. Dose—response studies using the pure compounds indicated that caffeic acid was the most active antioxidant with an IC50 < l μmol/l for copper-initiated low-density lipoprotein oxidation. Caffeic acid (1 μmol/l) significantly inhibited lipid hydroperoxide formation while sparing α-tocopherol consumption. Caffeic acid at the same concentration also inhibits aqueous peroxyl radical-induced oxidation of low-density lipoprotein, sparing α-tocopherol. There was no evidence of caffeic acid preventing the binding of copper to low-density lipoprotein.
4. We conclude that phenolics in both alcoholic and non-alcoholic beverages can give dose-dependent protection against oxidation of low-density lipoprotein. Caffeic acid and protocatechuic acid are two compounds likely to contribute to these effects. These findings may be relevant to the putative cardiovascular-protective effects of high phenolic content alcoholic beverages such as red wine; however, the widespread occurrence of antioxidants such as caffeic acid in fruits and vegetables suggests that these protective principles are not limited to red wine.
Antioxidant activity of ferulic acid beta-glucuronide, which is prepared from the plasma of feruloyl arabinose fed rats, in the CuSO4- induced LDL autoxidation system was studied. It has been found that absorbed ferulic acid occurred as the beta-glucuronide and that the antioxidant activity of ferulic acid beta-glucuronide, which has not only the hydrophobic ferulic acid moiety but also a hydrophilic sugar moiety, is stronger than ferulic acid in the LDL oxidation system.
Wheat bran contains several ester-linked dehydrodimers of ferulic acid, which were detected and quantified after sequential alkaline hydrolysis. The major dimers released were: trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2, 3- dihydrobenzofuran-3-carboxylic acid (5-8-BendiFA), (Z)-beta-[4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy]-4-hydroxy-3-methox ycinnamic acid (8-O-4-diFA) and (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid (5-5-diFA). trans-7-hydroxy-1-(4-hydroxy-3methoxyphenyl)-6-methoxy-1,2-dihydro - naphthalene-2,3-dicarboxylic acid (8-8-diFA cyclic form) and 4,4'-dihydroxy-3,3'-dimethoxy-beta,beta'-bicinnamic acid (8-8-diFA non cyclic form) were not detected. One of the most abundant dimers, 8-O-4-diFA, was purified from de-starched wheat bran after alkaline hydrolysis and preparative HPLC. The resultant product was identical to the chemically synthesised 8-O-4-dimer by TLC and HPLC as confirmed by 1H-NMR and mass spectrometry. The absorption maxima and absorption coefficients for the synthetic compound in ethanol were: lambda max: 323 nm, lambda min: 258 nm, epsilon lambda max (M-1 cm-1): 24,800 +/- 2100 and epsilon 280 (M-1 cm-1): 19,700 +/- 1100. The antioxidant properties of 8-O-4-diFA were assessed using: (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes and; (b) scavenging of the radical cation of 2,2'-azinobis (3-ethyl-benzothiazoline-6-sulphonate) (ABTS) relative to the water-soluble vitamin E analogue, Trolox C. The 8-O-4-diFA was a better antioxidant than ferulic acid in both lipid and aqueous phases. This is the first report of the antioxidant activity of a natural diferulate obtained from a plant.
The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2'-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids.
French maritime pine (Pinus maritima) bark extract (PBE) is a polyphenol-rich food supplement patented under the name of Pycnogenol and known to have strong antioxidant activity and different beneficial effects on human health. Although its biological properties have begun to be extensively studied both in vitro, in laboratory animals and more recently in humans, little is known about its bioavailability. The present study investigated the urinary excretion of free and conjugated ferulic acid, present in quantitatively detectable amounts in PBE, after oral PBE administration to human subjects. Eleven healthy adult subjects (4 women and 7men) consumed either a single dose (200 mg PBE) or two doses of PBE (100 and 200 mg, respectively) within a 48-h interval. Two days before the oral administration of PBE and during the urine sample collection period volunteers adhered to a diet low in polyphenols. Aliquots of all urine production were collected over 24 h. Free and conjugated ferulic acid was assessed in urine by HPLC using diode array detection. A close association between the dietary intake