Phenolic compounds in raw and cooked rice (Oryza sativa L.) and their inhibitory effect on the activity of angiotensin I-converting enzyme

Whole rice has been widely studied due to the abundance of bioactive compounds in its pericarp. Some of the beneficial effects of these compounds on human health have been attributed to their antioxidant and other biological activities, such as enzyme inhibition. In this work, we evaluated the contents of total, soluble and insoluble phenolic compounds of 6 red and 10 non-pigmented genotypes of whole rice as well as their inhibitory effect on the activity of angiotensin I-converting enzyme (ACE). The effects of cooking on phenolics and their inhibitory activities were also investigated. Red genotypes showed high content of phenolics, mainly soluble compounds, at an average of 409.7 mg ferulic acid eq./100 g, whereas overall lower average levels (99.4 mg ferulic acid eq./100 g) at an approximate soluble/insoluble compound ratio of 1:1 were observed in non-pigmented rice. Pigmented rice displayed a greater inhibitory effect on ACE than non-pigmented rice. In fact, a significant correlation between the content of soluble phenolics and ACE inhibition was observed (r = 0.8985, p < 0.05). In addition to significantly reducing the levels of total phenolics and ACE inhibition, cooking altered the soluble/insoluble compound ratio, especially among red rice genotypes. (C) 2011 Elsevier Ltd. All rights reserved.

EFFECT OF THERMAL TREATMENT ON PHENOLIC COMPOUNDS AND FUNCTIONALITY LINKED TO TYPE 2 DIABETES AND HYPERTENSION MANAGEMENT OF PERUVIAN AND BRAZILIAN BEAN CULTIVARS (PHASEOLUS VULGARIS L.) USING IN VITRO METHODS

The effect of thermal treatment on phenolic compounds and type 2 diabetes functionality linked to alpha-glucosidase and alpha-amylase inhibition and hypertension relevant angiotensin I-converting enzyme (ACE) inhibition were investigated in selected bean (Phaseolus vulgaris L,) cultivars from Peru and Brazil using in vitro models. Thermal processing by autoclaving decreased the total phenolic content in all cultivars, whereas the 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity-linked antioxidant activity increased among Peruvian cultivars, alpha-Amylase and alpha-glucosidase inhibitory activities were reduced significantly after heat treatment (73-94% and 8-52%, respectively), whereas ACE inhibitory activity was enhanced (9-15%). Specific phenolic acids such as chlorogenic and caffeic acid increased moderately following thermal treatment (2-16% and 5-35%, respectively). No correlation was found between phenolic contents and functionality associated to antidiabetes and antihypertension potential, indicating that non phenolic compounds may be involved. Thermally processed bean cultivars are interesting sources of phenolic acids linked to high antioxidant activity and show potential for hypertension prevention.

Comparative study of phenolic compounds in different Brazilian rice (Oryza sativa L.) genotypes

This study was conducted to evaluate the natural variability of total, extractable and non-extractable phenolics in pigmented and non-pigmented rice genotypes (Oryza sativa L.) and to estimate whether the contents and distribution of these compounds are typical for genotypes from indica and japonica subspecies. Twenty-one samples of commercial as well as new genotypes of brown rice, including seven pigmented genotypes were obtained from two Agronomic Institutes in South Brazil. Free and conjugated phenolics were extracted with ethanol, while bound phenolics were released by alkaline hydrolysis. Total phenolics were estimated in both fractions by the Folin-Ciocalteau method. Genotypes from Japonica and indica non-pigmented subspecies were not statistically distinguishable from each other, but differences in phenolic contents were associated with pericarp color. Despite individual differences, total phenolics were four times higher in pigmented than in non-pigmented genotypes (4246 and 1073 mg ferulic acid equiv. kg(-1), respectively). These high amounts were mostly due to the presence of extractable (free and conjugated) phenolics, which comprised up to 81% of total phenolics for pigmented genotypes. Non-extractable (bound) phenolics comprised 40% of total phenolics of non-pigmented rice genotypes while pigmented genotypes presented greater absolute amounts, but their contribution on total phenolics was small. (C) 2008 Elsevier Inc. All rights reserved.

Effect of Different Cooking Conditions on Phenolic Compounds and Antioxidant Capacity of Some Selected Brazilian Bean (Phaseolus vulgaris L.) Cultivars

The effects of different cooking conditions such as soaking, atmospheric (100 degrees C) or pressure boiling (121 degrees C), and draining of cooking water following thermal treatment on phenolic compounds and the DPPH radical scavenging capacity from two selected Brazilian bean cultivars (black and yellow-brown seed coat color) were investigated using a factorial design (2(3)). Factors that significantly reduced the total phenolic contents and antioxidant capacity in both cultivars were the soaking and draining stage. Independent of cooking temperature, total phenolics and antioxidant capacities were enhanced in treatments without soaking and where cooking water was not discarded, and this was likely linked to an increase of specific phenolic compounds detected by high performance liquid chromatography such as flavonols and free phenolic acids in both cultivars. Cooking of beans either at 100 or 121 degrees C, without a soaking stage and keeping the cooking water, would be recommendable for retaining antioxidant phenolic compounds.

Chemical characterization, bioactive compounds, and antioxidant capacity of jussara (Euterpe edulis) fruit from the Atlantic Forest in southern Brazil

Samples of fruit from the jussara palm plant (Euterpe edulis), collected in different regions of the state of Santa Catarina. Brazil, were analyzed for chemical composition. phenolic acids. anthocyanins, flavonoids and fatty acids profile. Results indicated that the jussara fruit has a high lipid content (18.45-44.08%), oleic acid (44.17-55.61%) and linoleic acid (18.19-25.36%) are the fatty acids found in the highest proportion, and other components were proteins (5.13-8.21%). ash (1.55-3.32%) and moisture (34.95-42.47%). Significant differences were found in the total phenolic, total monomeric anthocyanins and other flavonoids for the samples from the five cultivation regions. The fruit from region E harvested in summer, with high temperatures and medium altitudes, had the highest contents of total phenolics (2610.86 +/- 3.89 mg 100 g(-1) GAE) and monomeric anthocyanins (1080.54 +/- 2.33 mg 100g(-1) cy-3-glu). The phenolic compound included ferulic, gallic, hydroxybenzoic and p-coumaric acids, as well as catechin, epicatechin and quercetin. The results show promising perspectives for the exploitation of this tropical fruit with a chemical composition comprising considerable phenolic acids and flavonoids compounds and showing activity antioxidant. (C) 2010 Published by Elsevier Ltd.

Functionality of bioactive compounds in Brazilian strawberry (Fragaria x ananassa Duch.) cultivars: Evaluation of hyperglycemia and hypertension potential using in vitro models

Fruits of seven fully ripened strawberry cultivars grown in Brazil (Dover, Camp Dover, Camarosa, Sweet Charlie, Toyonoka, Oso Grande, and Piedade) were evaluated for total phenolics, antioxidant activity based on DPPH radical scavenging assay, and functionality such as inhibition of alpha-amylase, alpha-glucosidase, and angiotensin I-converting enzyme (ACE) relevant for potentially managing hyperglycemia and hypertension. The total phenolics content ranged from 966 to 1571 mu g of gallic acid/g of fruit fresh weight for Toyonoka and Dover, respectively. No correlation was found between total phenolics and antioxidant activity. The major phenolic compounds in aqueous extracts of strawberries were ellagic acid, quercetin, and chlorogenic acid. Strawberries had high alpha-glucosidase inhibitory activity. However, alpha-amylase inhibitory activity was very low in all cultivars. This suggested that strawberries could be considered as a potential dietary source with anti-hyperglycemic potential. The evaluated cultivars had no significant ACE inhibitory activity, reflecting low anti-hypertensive potential.

Bioactive compounds and quantification of total ellagic acid in strawberries (Fragaria x ananassa Duch.)

Strawberries are one of the most popular edible fruits in Brazil and their consumption has increased with the development of new varieties available at almost all seasons. Fruit of seven full-ripened strawberry cultivars (Dover, Camp Dover, Camarosa, Sweet Charlie, Toyonoka, Oso Grande and Piedade) were characterized in relation to the total phenolics, vitamin C, flavonoids, free and total ellagic acid contents and antioxidant capacity. Camp Dover had the lowest values for anthocyanins and total phenolics but the highest total flavonoid content. Dover presented the highest anthocyanin, total phenolics and ellagic acid contents and also elevated antioxidant capacity. The best conditions for the determination of the total ellagic acid content in strawberries were also optimized and the results showed that the extraction with 80% acetone, and hydrolysis using 2 N TFA at 120 degrees C for 60 min allowed a 99% recovery. (C) 2007 Elsevier Ltd. All rights reserved.

Effect of n-3 fatty acids and statins on oxidative stress in statin-treated hypercholestorelemic and normocholesterolemic women

Introduction: Although the combination of statins with n-3 fatty acids seems to be beneficial under the lipid profile aspect, there is little information about the interaction of these two compounds on oxidative stress. Objective: Evaluate the interaction between statins and n-3 fatty acids on oxidative stress in women, using a 2(2) factorial design. Methods: Forty-three women participated in this crossover design. They were separated into two groups in which 20 were under statin treatment for more than 6 months, and 23 were normolipidemic. Within each group, half of the patients received capsules containing 2.4 g/day of a mixture of EPA and DHA for 6 weeks, while the other half received a mixture of soya and corn oil. After a period of 90 days of washout, the groups were switched, and received the supplementation for 6 weeks more. Results: Statins reduced serum LDL and increased SOD expression. n-3 fatty acids increased the plasma malondialdehyde and SOD activity but reduced catalase expression (p < 0.05). The interaction involving statins and n-3 fatty acids was nearly significant to the serum triacylglycerol reduction (p = 0.054). Conclusion: Combining statins and n-3 fatty acids is an excellent strategy to reduce plasma cholesterol and triacylglycerol concentration in women. However, n-3 fatty acids increased the oxidative stress and the pleiotropic effect of statins seemed to be not enough to counterbalance this result. Our data also suggested that the mechanism by which n-3 fatty acids interfere in oxidative stress can be associated with antioxidant enzymes expression and activity. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

Effect of Toasting Intensity at Cooperage on Phenolic Compounds in Acacia (Robinia pseudoacacia) Heartwood

The phenolic composition of heartwood from Robinia pseudoacacia, commonly known as false acacia, before and after toasting in cooperage was studied by HPLC-DAD and HPLC-DAD/ESI-MS/MS. A total of 41 flavonoid and nonflavonoid compounds were identified, some tentatively, and quantified. Seasoned acacia wood showed high concentrations of flavonoid and low levels of nonflavonoid compounds, the main compounds being the dihydroflavonols dihydrorobinetin, fustin, tetrahydroxy, and trihydroxymethoxy dihydroflavonol, the flavonol robinetin, the flavanones robtin and butin, and a leucorobinetinidin, none of which are found in oak wood. The low molecular weight (LMW) phenolic compounds present also differed from those found in oak, since compounds with a beta-resorcylic structure, gallic related compounds, protocatechuic aldehyde, and some hydroxycinnamic compounds are included, but only a little gallic and ellagic acid. Toasting changed the chromatographic profiles of extracts spectacularly. Thus, the toasted acacia wood contributed flavonoids and condensed tannins (prorobinetin type) in inverse proportion to toasting intensity, while LMW phenolic compounds were directly proportional to toasting intensity, except for gallic and ellagic acid and related compounds. Even though toasting reduced differences between oak and acacia, particular characteristics of this wood must be taken into account when considering its use in cooperage: the presence of flavonoids and compounds with beta-resorcylic structure and the absence of hydrolyzable tannins.

Evaluation of natural and synthetic compounds according to their antioxidant activity using a multivariate approach

The antioxidant activity of natural and synthetic compounds was evaluated using five in vitro methods: ferric reducing/antioxidant power (FRAP), 2,2-diphenyl-1-picrylhydradzyl (DPPH), oxygen radical absorption capacity (ORAL), oxidation of an aqueous dispersion of linoleic acid accelerated by azo-initiators (LAOX), and oxidation of a meat homogenate submitted to a thermal treatment (TBARS). All results were expressed as Trolox equivalents. The application of multivariate statistical techniques suggested that the phenolic compounds (caffeic acid, carnosic acid, genistein and resveratrol), beyond their high antioxidant activity measured by the DPPH, FRAP and TBARS methods, showed the highest ability to react with the radicals in the ORAC methodology, compared to the other compounds evaluated in this study (ascorbic acid, erythorbate, tocopherol, BHT, Trolox, tryptophan, citric acid, EDTA, glutathione, lecithin, methionine and tyrosine). This property was significantly correlated with the number of phenolic rings and catecholic structure present in the molecule. Based on a multivariate analysis, it is possible to select compounds from different clusters and explore their antioxidant activity interactions in food products.

Bioequivalence Evaluation of Single Doses of Two Tramadol Formulations: A Randomized, Open-Label, Two-Period Crossover Study in Healthy Brazilian Volunteers

Background: Tramadol is a well tolerated and effective analgesic used to treat moderate to severe pain. Several generic formulations of tramadol are available in Brazil; however, published information regarding their bioequivalence in the Brazilian population is not available. A study was designed for Brazilian regulatory authorities to allow marketing of a generic formulation. Objective: The purpose of this study was to compare the bioequivalence of 2 commercial tablet preparations containing tramadol 100 mg marketed for use in Brazil. Methods: A randomized, open-label, 2 x 2 crossover study was performed in healthy Brazilian volunteers under fasting conditions with a washout period of 12 days. Two tablet formulations of tramadol 100 mg (test and reference formulations) were administered as a single oral dose, and blood samples were collected over 24 hours. Tramadol plasma concentrations were quantified using a validated HPLC method. A plasma concentration time profile was generated for each volunteer and then mean values were determined, from which C(max), T(max), AUC(0-t), AUC(0-infinity), k(e), and t(1/2) were calculated using a noncompartmental model. Bioequivalence between the products was determined by calculating 90% CIs for the ratios of C(max), AUC(0-t), and AUC(0-infinity) values for the test and reference products using log-transformed data. Tolerability was assessed by monitoring vital signs (temperature, blood pressure, heart rate), laboratory tests (hematology, blood biochemistry, hepatic function, urinalysis), and interviews with the volunteers before medication administration and every 2 hours during the study. Results: Twenty-six healthy volunteers (13 men, 13 women) were enrolled in and completed the study. Mean (SD) age was 30 (6.8) years (range, 21-44 years), mean weight was 64 (8.3) kg (range, 53-79 kg), and mean height was 166 (6.4) cm (range, 155-178 cm). The 90% CIs for the ratios of C(max) (1.01-1.17), AUC(0-t) (1.00-1.13), and AUC(0-infinity) (1.00-1.14) values for the test and reference products fell within the interval of 0.80 to 1.25 proposed by most regulatory agencies, including the Brazilian regulatory body. No clinically important adverse effects were reported; only mild somnolence was reported by 4 volunteers and mild headaches by 5 volunteers, and there was no need to use medication to treat these symptoms. Conclusion: Pharmacokinetic analysis in these healthy Brazilian volunteers suggested that the test and reference formulations of tramadol 100-mg tablets met the regulatory requirements to assume bio-equivalence based on the Brazilian regulatory definition. (Clin Ther 2010;32:758-765) (C) 2010 Excerpta Medica Inc.

Characterization of Brazilian lager and brown ale beers based on color, phenolic compounds, and antioxidant activity using chemometrics

BACKGROUND: Epidemiological studies have shown that beer has positive effects on inhibiting atherosclerosis, decreasing the content of serum low-density lipoprotein cholesterol and triglycerides, by acting as in vivo free radical scavenger. In this research, the antioxidant activity of commercial Brazilian beers (n = 29) was determined by the oxygen radical absorbance capacity (ORAC) and 1,1 -diphenyl-2-picrylhydrazyl (DPPH(center dot)) assays and results were analyzed by chemometrics. RESULTS: The brown ale samples (n = 11) presented higher (P < 0.05) flavonoids (124.01 mg L(-1)), total phenolics (362.22 mg L(-1)), non-flavonoid phenolics (238.21 mg L(-1)), lightness (69.48), redness (35.75), yellowness (55.71), color intensity (66.86), hue angle (59.14), color saturation (0.9620), DPPH(center dot) values (30.96% inhibition), and ORAC values (3,659.36 mu mol Trolox equivalents L(-1)), compared to lager samples (n = 18). Brown ale beers presented higher antioxidant properties (P < 0.05) measured by ORAC (1.93 times higher) and DPPH (1.65 times higher) compared to lager beer. ORAC values correlated well with the content of flavonoids (r = 0.47; P = 0.01), total phenolic compounds (r = 0.44; P < 0.01) and DPPH (r = 0.67; P < 0.01). DPPH values also correlated well to the content of flavonoids (r = 0.69; P < 0.01), total phenolic compounds (r = 0.60; P < 0.01), and non-flavonoid compounds (r = 0.46; P = 0.01). CONCLUSION: The results suggest that brown ale beers, and less significantly lager beers, could be sources of bioactive compounds with suitable free radical scavenging properties. (C) 2010 Society of Chemical Industry

Homocoupling reactions of alkynes, alkenes and alkyl compounds

FAPESP[07/5904-2]

Phenolic compounds content and antioxidant activity in pomace from selected red grapes (Vitis vinifera L. and Vitis labrusca L.) widely produced in Brazil

The phenolic compounds content and antioxidant activity of pomace from the vinification of grape varieties widely produced in Brazil (Cabernet Sauvignon, Merlot, Bordeaux and Isabel) were investigated with a view to their exploitation as a potential source of natural antioxidants. Cabernet Sauvignon grape pomace was found to have the highest content of total phenolic compounds (74.75 mg gallic acid equivalent (GAE)/g), the highest antioxidant activity (determined using the 2,2`-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging methods; 485.42 and 505.52 mu Mol Trolox equivalent antioxidant capacity (TEAC)/g, respectively), and the highest reducing power (determined using the FRAP method; 249.46 mu Mol TEAC/g). The Bordeaux variety showed the highest oxidation inhibition power (41.13%), determined using the beta-carotene/linoleic acid method and the highest content of total anthocyanins (HPLC; 29.17 mg/g). Catechin was the most abundant non-anthocyanic compound identified in the grape pomace (150.16 mg/100 g) for all varieties. In this study, pomaces of the red wine vinification of Cabernet Sauvignon and Bordeaux varieties showed the highest potential as a source of antioxidant compounds and natural colourants, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

Antimicrobial compounds produced by Lactobacillus sakei subsp sakei 2a, a bacteriocinogenic strain isolated from a Brazilian meat product

Bacteriocins produced by lactic acid bacteria are gaining increased importance due to their activity against undesirable microorganisms in foods. In this study, a concentrated acid extract of a culture of Lactobacillus sakei subsp. sakei 2a, a bacteriocinogenic strain isolated from a Brazilian pork product, was purified by cation exchange and reversed-phase chromatographic methods. The amino acid sequences of the active antimicrobial compounds determined by Edman degradation were compared to known protein sequences using the BLAST-P software. Three different antimicrobial compounds were obtained, P1, P2 and P3, and mass spectrometry indicated molecular masses of 4.4, 6.8 and 9.5 kDa, respectively. P1 corresponds to classical sakacin P, P2 is identical to the 30S ribosomal protein S21 of L. sakei subsp. sakei 23 K, and P3 is identical to a histone-like DNA-binding protein HV produced by L. sakei subsp. sakei 23 K. Total genomic DNA was extracted and used as target DNA for PCR amplification of the genes sak, lis and his involved in the synthesis of P1, P2 and P3. The fragments were cloned in pET28b expression vector and the resulting plasmids transformed in E. coli KRX competent cells. The transformants were active against Listeria monocytogenes, indicating that the activity of the classical sakacin P produced by L. sakei 2a can be complemented by other antimicrobial proteins.