Critical stages of the brewing process for changes in antioxidant activity and levels of phenolic compounds in ale

Samples were taken at each stage of brewing (malt, milling, mashing, wort separation, hop addition, boiling, whirlpool, dilution, fermentation, warm rest, chill-lagering, beer filtration, carbonation and bottling, pasteurization, and storage). The level of antioxidant activity of unfractionated, low-molecular-mass (LMM) and high-molecular-mass (HMM) fractions was measured by the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfortic acid) radical cation (ABTS(.+)) and ferric-reducing antioxidant power (FRAP) procedures. Polyphenol levels were assessed by HPLC. The LMM fraction (<5 kDa) was responsible for similar to80% of the level of antioxidant activity of the unfractionated malt and beer samples. In the unfractionated samples, significant decreases (P < 0.001) in antioxidant activity levels were observed after milling and beer filtration, with the decrease after beer filtration being accompanied by a significant decrease (P > 0.001) in catechin and ferulic acid levels. Increases in antioxidant activity levels were observed after mashing, boiling, fermentation, chill-lagering, and pasteurization, in line with previous studies on lager. Additionally, increases in the level of antioxidant activity occurred after wort separation and carbonation and bottling and were accompanied by increases in levels of most monitored polyphenols. Data from the ABTS(.-) and FRAP assays indicated that the compounds contributing to the levels of antioxidant activity responded differently in the two procedures. Levels of ferulic, vanillic, and chlorogenic acids and catechin accounted for 45-61% of the variation in antioxidant activity levels.

Effect of heat treatment on the antioxidant activity, color, and free phenolic acid profile of malt

Green malt was kilned at 95 degrees C following two regimens: a standard regimen (SKR) and a rapid regimen (RKR). Both resulting malts were treated further in a tray dryer heated to 120 degrees C, as was green malt previously dried to 65 degrees C (TDR). Each regimen was monitored by determining the color, antioxidant activity (by both ABTS(center dot+) and FRAP methods), and polyphenolic profile. SKR and RKR malts exhibited decreased L* and increased b* values above approximately 80 degrees C. TDR malts changed significantly less, and color did not develop until 110 degrees C, implying that different chemical reactions lead to color in those malts. Antioxidant activity increased progressively with each regimen, although with TDR malts this became significant only at 110-120 degrees C. The RKR malt ABTS(center dot+) values were higher than those of the SKR malt. The main phenolics, that is, ferulic, p-coumaric, and vanillic acids, were monitored throughout heating. Ferulic acid levels increased upon heating to 80 degrees C for SKR and to 70 degrees C for RKR, with subsequent decreases. However, the levels for TDR malts did not increase significantly. The increase in free phenolics early in kilning could be due to enzymatic release of bound phenolics and/or easier extractability due to changes in the matrix. The differences between the kilning regimens used suggest that further modification of the regimens could lead to greater release of bound phenolics with consequent beneficial effects on flavor stability in beer and, more generally, on human health.

In vitro fermentation of a red wine extract by human gut microbiota: changes in microbial groups and formation of phenolic metabolites

An in vitro batch culture fermentation experiment was conducted with fecal inocula from three healthy volunteers in the presence and absence of a red wine extract. Changes in main bacterial groups were determined by FISH during a 48 h fermentation period. The catabolism of main flavonoids (i.e., flavan-3-ols and anthocyanins) and the formation of a wide a range of phenolic microbial metabolites were determined by a targeted UPLC-PAD-ESI-TQ MS method. Statistical analysis revealed that catechol/pyrocatechol, as well as 4-hydroxy-5-(phenyl)-valeric, 3- and 4-hydroxyphenylacetic, phenylacetic, phenylpropionic, and benzoic acids, showed the greatest increases in concentration during fermentation, whereas 5-(3′-hydroxyphenyl)-γ-valerolactone, its open form 4-hydroxy-5-(3′-hydroxyphenyl)-valeric acid, and 3,4-dihydroxyphenylacetic acid represented the largest interindividual variations in the catabolism of red wine polyphenols. Despite these changes, microbial catabolism did not produce significant changes in the main bacterial groups detected, although a slight inhibition of the Clostridium histolyticum group was observed.

Phenolic profile of Sercial and Tinta Negra Vitis vinifera L. grape skins by HPLC–DAD–ESI-MSn: novel phenolic compounds in Vitis vinifera L. grape

This study represents the first phytochemical research of phenolic components of Sercial and Tinta Negra Vitis vinifera L. The phenolic profiles of Sercial and Tinta Negra V. vinifera L. grape skins (white and red varieties, respectively) were established using high performance liquid chromatography–diode array detection–electrospray ionisation tandem mass spectrometry (HPLC–DAD–ESI-MSn), at different ripening stages (véraison and maturity). A total of 40 phenolic compounds were identified, which included 3 hydroxybenzoic acids, 8 hydroxycinnamic acids, 4 flavanols, 5 flavanones, 8 flavonols, 4 stilbenes, and 8 anthocyanins. For the white variety, in both ripening stages, hydroxycinnamic acids and flavonols were the main phenolic classes, representing about 80% of the phenolic composition. For red variety, at véraison, hydroxycinnamic acids and flavonols were also the predominant classes (71%), but at maturity, anthocyanins represented 84% of the phenolic composition. As far as we know, 10 compounds were reported for the first time in V. vinifera L. grapes, namely protocatechuic acid-glucoside, p-hydroxybenzoyl glucoside, caftaric acid vanilloyl pentoside, p-coumaric acid-erythroside, naringenin hexose derivate, eriodictyol-glucoside, taxifolin-pentoside, quercetin-glucuronide-glucoside, malylated kaempferol-glucoside, and resveratrol dimer. These novel V. vinifera L. grape components were identified based on their MSn fragmentation profile. This data represents valuable information that may be useful to oenological management and to valorise these varieties as sources of bioactive compounds.

Development of a novel microextraction by packed sorbent-based approach followed by ultrahigh pressure liquid chromatography as a powerful technique for quantification phenolic constituents of biological interest in wines

A novel analytical approach, based on a miniaturized extraction technique, the microextraction by packed sorbent (MEPS), followed by ultrahigh pressure liquid chromatography (UHPLC) separation combined with a photodiode array (PDA) detection, has been developed and validated for the quantitative determination of sixteen biologically active phenolic constituents of wine. In addition to performing routine experiments to establish the validity of the assay to internationally accepted criteria (linearity, sensitivity, selectivity, precision, accuracy), experiments are included to assess the effect of the important experimental parameters on the MEPS performance such as the type of sorbent material (C2, C8, C18, SIL, and M1), number of extraction cycles (extract-discard), elution volume, sample volume, and ethanol content, were studied. The optimal conditions of MEPS extraction were obtained using C8 sorbent and small sample volumes (250 μL) in five extraction cycle and in a short time period (about 5 min for the entire sample preparation step). The wine bioactive phenolics were eluted by 250 μL of the mixture containing 95% methanol and 5% water, and the separation was carried out on a HSS T3 analytical column (100 mm × 2.1 mm, 1.8 μm particle size) using a binary mobile phase composed of aqueous 0.1% formic acid (eluent A) and methanol (eluent B) in the gradient elution mode (10 min of total analysis). The method gave satisfactory results in terms of linearity with r2-values > 0.9986 within the established concentration range. The LOD varied from 85 ng mL−1 (ferulic acid) to 0.32 μg mL−1 ((+)-catechin), whereas the LOQ values from 0.028 μg mL−1 (ferulic acid) to 1.08 μg mL−1 ((+)-catechin). Typical recoveries ranged between 81.1 and 99.6% for red wines and between 77.1 and 99.3% for white wines, with relative standard deviations (RSD) no larger than 10%. The extraction yields of the MEPSC8/UHPLC–PDA methodology were found between 78.1 (syringic acid) and 99.6% (o-coumaric acid) for red wines and between 76.2 and 99.1% for white wines. The inter-day precision, expressed as the relative standard deviation (RSD%), varied between 0.2% (p-coumaric and o-coumaric acids) and 7.5% (gentisic acid) while the intra-day precision between 0.2% (o-coumaric and cinnamic acids) and 4.7% (gallic acid and (−)-epicatechin). On the basis of analytical validation, it is shown that the MEPSC8/UHPLC–PDA methodology proves to be an improved, reliable, and ultra-fast approach for wine bioactive phenolics analysis, because of its capability for determining simultaneously in a single chromatographic run several bioactive metabolites with high sensitivity, selectivity and resolving power within only 10 min. Preliminary studies have been carried out on 34 real whole wine samples, in order to assess the performance of the described procedure. The new approach offers decreased sample preparation and analysis time, and moreover is cheaper, more environmentally friendly and easier to perform as compared to traditional methodologies.

Fatty acids and bioactive compounds of the pulps and kernels of Brazilian palm species, guariroba (Syagrus oleraces), jeriva (Syagrus romanzoffiana) and macauba (Acrocomia aculeata)

BACKGROUND: Bioactive compounds are capable of providing health benefits, reducing disease incidence or favoring body functioning. There is a growing search for vegetable oils containing such compounds. This study aimed to characterize the pulp and kernel oils of the Brazilian palm species guariroba (Syagrus oleracea), jeriva (Syagrus romanzoffiana) and macauba (Acrocomia aculeata), aiming at possible uses in several industries.RESULTS: Fatty acid composition, phenolic and carotenoid contents, tocopherol composition were evaluated. The majority of the fatty acids in pulps were oleic and linoleic; macauba pulp contained 526 g kg(-1) of oleic acid. Lauric acid was detected in the kernels of all three species as the major saturated fatty acid, in amounts ranging from 325.8 to 424.3 g kg(-1). The jeriva pulp contained carotenoids and tocopherols on average of 1219 mu g g(-1) and 323.50 mg kg(-1), respectively.CONCLUSION: The pulps contained more unsaturated fatty acids than the kernels, mainly oleic and linoleic. Moreover, the pulps showed higher carotenoid and tocopherol contents. The kernels showed a predominance of saturated fatty acids, especially lauric acid. The fatty acid profiles of the kernels suggest that these oils may be better suited for the cosmetic and pharmaceutical industries than for use in foods. (C) 2011 Society of Chemical Industry

Phenolic Composition of the Brazilian Seedless Table Grape Varieties BRS Clara and BRS Morena

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Phenolic Derivatives from Fruits of Dipteryx lacunifera DUCKE and Evaluation of Their Antiradical Activities

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Evaluating of the activity antioxidant and fatty acids profile of lychee seeds (Litchi chinensis SONN.)

Purpose: The purpose of this paper is to characterize lychee seeds regarding their centesimal composition, and also to evaluate their antioxidant potential and fatty acid profile. Design/methodology/approach: To obtain the extract, dehydrated and grinded seeds were extracted with ethyl alcohol for 30 min, at a proportion of 1:3 of seeds:ethyl alcohol, under continuous agitation, at room temperature. Afterwards, the mixture was filtered and the supernatant subjected to a rotoevaporator at 40oC aiming to determine, by direct weighing, the extract dry matter yield. Findings: The largest found values went to the total carbohydrates (72.75 percent). In the oil from the lychee seeds there was a high percentage of unsaturated fatty acids, the main component being linoleic, considered an essential fatty acid. Research limitations/implications: Implies the identification of compounds biativos extracted from seeds of tropical and subtropical fruits, and to prevent certain types of diseases. Originality/value: The article tries to identify new source of phenolic compounds extracted from fruit. © Emerald Group Publishing Limited.

Antioxidant capacity and total phenolic content of hydrothermally-treated 'Fuerte' avocado

Avocados possess high nutritional value with proven effectiveness in preventing cardiovascular diseases, attributed primarily to their unsaturated fatty acids content. This fruit is also rich in carotenoids and vitamins, particularly vitamin E. This work evaluates the antioxidant capacity and total phenolic content of hydrothermally-treated Fuerte avocado. Fruits were selected and hydrothermally treated at 45°C for 5, 10, 15 and 20 min. They were then stored in a refrigerator (10 ± 10°C and 90±5% relative humidity) and evaluated over a 15-day period. The total phenolic content increased up to the sixth day of storage, and decreased thereafter, without differences between the treatments. The percentage of antioxidant capacity of the control and the hydrothermally-treated samples for 5 and 10 min increased during storage. Untreated fruits showed the highest percentage of antioxidant capacity. However, the antioxidant capacity of avocado fruits subjected to these treatments declined starting on the twelfth day of storage, possibly due to the fruits' senescence. Hydrothermal treatments for 15 and 20 min delayed fruit senescence while the antioxidant capacity continued to increase up to the fifteenth day of storage. No significant correlation was found between antioxidant capacity and total phenolic content. The antioxidant capacity of ripe Fuerte avocado was higher than that of unripe or overripe avocado.

Soursop (Annona muricata L.) and sugar apple (Annona squamosa L.): Antioxidant activity, fatty acids profile and determination of tocopherols

Purpose: This study aims to analyze the soursop and sugar apple seeds as to its composition, to evaluate the antioxidant potential of seeds extract and characterize the oil extracted from them, regarding the fatty acids profile and content of tocopherols. Design/methodology/approach: To obtain the extracts, dried and crushed seeds were extracted with ethanol for 30 minutes, at a ratio of 1:3 (m/m, seed: ethyl alcohol) under continuous stirring at room temperature. Then, the mixture was filtered and the supernatants subjected to rotoevaporator at 40°C aiming to determine, by direct weighing, the yields of dry extracts. Findings: According to the results, the soursop and sugar apple seeds constituted significant sources of lipids, proteins and carbohydrates and can therefore be used in food and feed, and offer relevant antioxidant activity of phenolic compounds. The oil seeds are a good source of unsaturated fatty acids, especially oleic and linoleic acids and they have significant amounts of total tocopherol. Research limitations/implications: Implications are the identification of bioactive compounds extracted from seeds of tropical and subtropical fruits, and to prevent certain types of diseases. Practical implications: The information presented might be directly used for developing of functional foods such as fruits. Originality/value: The article tries to identify new source of compounds extracted from fruits. © Emerald Group Publishing Limited.

Fatty acids and some antioxidant compounds of Psidium guajava seed oil

Physico-chemical characteristics, fatty acid and tocopherol compositions, total phenolic content and antioxidant activity of crude oil extracted from guava (Psidium guajava var. pomifera) seeds were investigated. Oil yield from the seeds was 14.0%. Data obtained for the analytical indexes compared well with those of others edible oils. The oil showed high levels of unsaturated fatty acids (88.1%), mainly linoleic acid (78.4%). The tocopherol and total phenolic contents in the oil amounted to 29.2 and 92.3 mg/100 g, respectively. The guava seed oil exhibited a great DPPH · scavenging activity showing EC₅₀ of 12.9 g oil/g [DPPH · ] -1 and antiradical efficiency of 7.9×10 -2 . Therefore, the potential utilization of the guava seed oil as a raw material of food, chemical and pharmaceutical industries appears to be favourable and provides the use of a renewable resource, adding value to agricultural products.

Phenolic composition of the berry parts of hybrid grape cultivar BRS Violeta (BRS Rubea×IAC 1398-21) using HPLC-DAD-ESI-MS/MS

The grape is considered a major source of phenolic compounds when compared to other fruits and vegetables, however, there are many cultivars with distinct characteristics directly linked to phenolic profile. Thus, the present study aimed to identify and quantify, for the first time and in detail, the phenolic compounds present in the skin, flesh and seeds of BRS Violeta grape berry using combination of SPE methodologies and analytical HPLC-DAD-ESI-MS/MS. The study was extended to the different berry parts and the most important grape and wine phenolic families, and has revealed interesting features. Violeta grape has a very thick skin (46% of grape weight) that accumulated the most of grape phenolic compounds: great amount of anthocyanins (3930. mg/kg, as malvidin 3,5-diglucoside), together with also important amounts of flavonols (150. mg/kg, as quercetin 3-glucoside), hydroxycinnamic acid derivatives (HCAD; 120. mg/kg, as caftaric acid), and proanthocyanidins (670. mg/kg, as (+)-catechin); in contrast, it seems to be a low resveratrol producer. Violeta grape seeds accounted for similar proportions of low molecular weight flavan-3-ols (mainly monomers; 345. mg/kg, as (+)-catechin) and proanthocyanidins (480. mg/kg, as (+)-catechin). Violeta grape is a teinturier cultivar, but it only contained traces of anthocyanins and low amounts of all the other phenolic types in its red-colored flesh. The anthocyanin composition of Violeta grape was dominated by anthocyanidin 3,5-diglucosides (90%). Within flavonols, myricetin-type predominated and kaempferol-type was missing. In addition to expected hydroxycinnamoyl-tartaric acids, several isomeric esters of caffeic and p-coumaric acids with hexoses were tentatively identified, accounting for relevant proportions within the pool of HCAD. Although pending of further confirmation over successive vintages, the aforementioned results suggest that BRS Violeta grape cultivar could be considered an interesting candidate for the elaboration of highly colored and antioxidant-rich grape juices and wines. © 2013 Elsevier Ltd.

CHEMICAL CONSTITUENTS FROM RED ALGAE Bostrychia radicans (Rhodomelaceae): NEW AMIDES AND PHENOLIC COMPOUNDS

This study describes the isolation and structural determination of two amides, isolated for the first time: N,4-dihydroxy-N-(2'-hydroxyethyl)-benzamide (0.019%) and N, 4-dihydroxy-N-(2'-hydroxyethyl)-benzeneacetamide (0.023%). These amides, produced by the red macroalgae Bostrychia radicans, had their structures assigned by NMR spectral data and MS analyses. In addition, this chemical study led to the isolation of cholesterol, heptadecane, squalene, trans-phytol, neophytadiene, tetradecanoic and hexadecanoic acids, methyl hexadecanoate and methyl 9-octadecenoate, 4-(methoxymethyl)-phenol, 4-hydroxybenzaldehyde, methyl 4-hydroxybenzeneacetate, methyl 2-hydroxy-3-(4-hydroxyphenyl)-propanoate, hydroquinone, methyl 4-hydroxymandelate, methyl 4-hydroxybenzoate, 4-hydroxybenzeneacetic acid and (4-hydroxyphenyl)-oxo-acetaldehyde. This is the first report concerning these compounds in B. radicans, contributing by illustrating the chemical diversity within the Rhodomelaceae family.

Antioxidant Activity of Brazilian Vegetables and Its Relation with Phenolic Composition

Vegetables are widely consumed in Brazil and exported to several countries. This study was performed to evaluate the phenolic content and antioxidant activity of vegetables commonly consumed in Brazil using five different methods, namely DPPH and ABTS free radical, beta-carotene bleaching, reduction of Fe3+ (FRAP), oxidative stability in Rancimat, and the chemical composition using gas chromatography-mass spectrometry (GC-MS). The content of phenolic compounds ranged from 1.2 mg GA/g (carrot) to 16.9 mg GA/g (lettuce). Vegetables presenting the highest antioxidant activity were lettuce (77.2 mu mol Trolox/g DPPH center dot; 447.1 mu mol F2+/g FRAP), turmeric (118.6 mu mol Trolox/g ABTS(center dot+); 92.8% beta-carotene), watercress and broccoli (protective factor 1.29-Rancimat method). Artichoke, spinach, broccoli, and asparagus also showed considerable antioxidant activity. The most frequent phenolic compounds identified by GC-MS were ferulic, caffeic, p-coumaric, 2-dihydroxybenzoic, 2,5-dihydroxybenzoic acids, and quercetin. We observed antioxidant activity in several vegetables and our results point out their importance in the diet.