Effect of the addition of soluble polysaccharides from red and white grape skins on the polyphenolic composition and sensory properties of Tempranillo red wines.

Soluble polysaccharides from white (PSW) and red (PSR) grape skins were obtained to be evaluated as potential modulators of the unbalanced astringency of a Tempranillo red wine. The modulation of astringency was evaluated by a sensory panel and it seemed to be related to the changes in the polyphenolic profile. Isothermal Titration Calorimetry (ITC) studies, employed to characterize flavan-3-ol-polysaccharide interactions, showed that PSR decreased noticeably wine astringency causing a great flavan-3-ol loss (ca. 40 %), since they interacted more spontaneously with the flavan-3-ols (ca. ΔGtotal = -2.14 × 104 cal/mol) than PSW (ca. ΔGtotal = -1.32 × 104 cal/mol). The strength of these interactions seems to be related to the polysaccharide molecular size and to the presence of arabinogalactans in the structure. On the contrary, PSW showed no relevant effects on wine astringency. Furthermore, potential variations of color were also assessed and no deleterious effect was observed after the addition of any polysaccharide.

Gastrointestinal fate of phenolic compounds and amino derivatives from the cocoa shell: An in vitro and in silico approach.

The objective of this study was to assess how in vitro gastrointestinal digestion influenced the bioaccessibility and potential bioavailability of phenolic compounds and methylxanthines in thecocoa shell (CS) in the form of flour (CSF) and aqueous extract (CSE). To comprehend how these phytochemicals behaved during gastrointestinal digestion, we also modeled in silico the colonic microbial biotransformation of the phenolic compounds in the CS. Different groups of phenolic compounds (mainly gallic andprotocatechuic acids, and catechin) and methylxanthines (theobromine and caffeine)could be found in the CS. Methylxanthines and phenolic compounds were released differently during gastrointestinal digestion. Whereas digestion triggered the release of hydroxybenzoic acids (67-73%) and flavan-3-ols (73-88%) during the intestinal phase, it also caused the degradation of flavonols and flavones. Besides, the release of phytochemicals was significantly influenced by the CS matrix type. Phenolic compounds were protected by the CSF matrix. Phenolic acids from CSF were more bioaccessible in the intestinal (1.2-fold, p < 0.05) and colonic (1.3-fold, p < 0.05) phases than those from the CSE. Methylxanthines were also more bioaccessible in the intestinal (1.8-fold, p < 0.01) and colonic phases (1.3-fold, p < 0.001) and bioavailable (1.8-fold, p < 0.001) in the CSF. Colonic metabolism demonstrated that the gut microbiota could biotransform non-absorbed phenolic compounds into other lower molecular weight and more bioavailable metabolites. These findings support the CS's potential as a source of bioaccessible, bioavailable, and active phytochemicals.

Selection of Enzymatic Treatments for Upcycling Lentil Hulls into Ingredients Rich in Oligosaccharides and Free Phenolics.

In this study, the comprehensive chemical characterization of red lentil hulls obtained from the industrial production of football and split lentils was described. The lentil hulls were rich in dietary fiber (78.43 g/100 g dry weight with an insoluble to soluble fiber ratio of 4:1) and polyphenols (49.3 mg GAE/g dry weight, of which 55% was bound phenolics), which revealed the suitability of this lentil by-product as a source of bioactive compounds with recognized antioxidant and prebiotic properties. The release of oligosaccharides and phenolic compounds was accomplished by enzymatic hydrolysis, microwave treatment and a combination of both technologies. The key role played by the selection of a suitable enzymatic preparation was highlighted to maximize the yield of bioactive compounds and the functional properties of the lentil hull hydrolysates. Out of seven commercial preparations, the one with the most potential for use in a commercial context was Pectinex® Ultra Tropical, which produced the highest yields of oligosaccharides (14 g/100 g lentil hull weight) and free phenolics (45.5 mg GAE/100 g lentil hull weight) and delivered a four-fold increase in terms of the original antioxidant activity. Finally, this enzyme was selected to analyze the effect of a microwave-assisted extraction pretreatment on the yield of enzymatic hydrolysis and the content of free phenolic compounds and oligosaccharides. The integrated microwave and enzymatic hydrolysis method, although it increased the solubilization yield of the lentil hulls (from 25% to 34%), it slightly decreased the content of oligosaccharides and proanthocyanidins and reduced the antioxidant activity. Therefore, the enzymatic hydrolysis treatment alone was more suitable for producing a lentil hull hydrolysate enriched in potential prebiotics and antioxidant compounds.

Understanding the Gastrointestinal Behavior of the Coffee Pulp Phenolic Compounds under Simulated Conditions.

Numerous residues, such as the coffee pulp, are generated throughout coffee processing. This by-product is a source of antioxidant phytochemicals, including phenolic compounds and caffeine. However, the antioxidant properties of the phenolic compounds from the coffee pulp are physiologically limited to their bioaccessibility, bioavailability, and biotransformation occurring during gastrointestinal digestion. Hence, this study explored the phenolic and caffeine profile in the coffee pulp flour (CPF) and extract (CPE), their intestinal bioaccessibility through in vitro digestion, and their potential bioavailability and colonic metabolism using in silico models. The CPE exhibited a higher concentration of phenolic compounds than the CPF, mainly phenolic acids (protocatechuic, chlorogenic, and gallic acids), followed by flavonoids, particularly quercetin derivatives. Caffeine was found in higher concentrations than phenolic compounds. The antioxidant capacity was increased throughout the digestive process. The coffee pulp matrix influenced phytochemicals' behavior during gastrointestinal digestion. Whereas individual phenolic compounds generally decreased during digestion, caffeine remained stable. Then, phenolic acids and caffeine were highly bioaccessible, while flavonoids were mainly degraded. As a result, caffeine and protocatechuic acid were the main compounds absorbed in the intestine after digestion. Non-absorbed phenolic compounds might undergo colonic biotransformation yielding small and potentially more adsorbable phenolic metabolites. These results contribute to establishing the coffee pulp as an antioxidant food ingredient since it contains bioaccessible and potentially bioavailable phytochemicals with potential health-promoting properties.

Applications of Natural Products in Food.

The term natural products includes any substance produced by living organisms [...].

Effects of different industrial processes on the phenolic composition of white and brown teff (Eragrostis tef (Zucc.) Trotter).

Teff is currently being incorporated into a range of foodstuffs, especially gluten-free flakes and extruded products. The main objective of this work was to assess the effects of different treatments (industrial milling, formation of flakes and extrusion) on the phenolic composition of two types of teff grains differing in their colour (white and brown). Fifty-nine phenolic compounds were detected by HPLC-DAD-MSn. C-glycosyl flavones accounted for more than 90% of the total phenolic contents in both teff types. White teff mostly contained apigenin-derived flavones (86-92%), whereas luteolin derivatives prevailed in brown teff (91-94%). The industrial processes, mainly flaking and extrusion, caused marked changes in the phenolic composition, some of which were dependent on the teff type. In both teff types, processing changed the phenolic profiles similarly by increasing C-monoglycosyl flavones and decreasing acylated derivatives. However, the total content was increased in flakes and extruded products made only from brown teff grains.

Agricultural and Food Waste: Analysis, Characterization and Extraction of Bioactive Compounds and Their Possible Utilization.

The characterization and reutilization of agricultural and food waste is an important strategy to ensure the sustainable development of the agricultural and food industries. As a result, the environmental impact of these industries can be reduced, thus contributing to the fight against environmental problems, mainly to those related to a potential mitigation of climatic change. This Special Issue includes five papers that reported important findings from research activities related to the reutilization of by-products from food processing industries, which help to increase the knowledge in this field.

Bioavailability of Melatonin from Lentil Sprouts and Its Role in the Plasmatic Antioxidant Status in Rats.

Melatonin is a multifunctional antioxidant neurohormone found in plant foods such as lentil sprouts. We aim to evaluate the effect of lentil sprout intake on the plasmatic levels of melatonin and metabolically related compounds (plasmatic serotonin and urinary 6-sulfatoxymelatonin), total phenolic compounds, and plasmatic antioxidant status, and compare it with synthetic melatonin. The germination of lentils increases the content of melatonin. However, the phenolic content diminished due to the loss of phenolic acids and flavan-3-ols. The flavonol content remained unaltered, being the main phenolic family in lentil sprouts, primarily composed of kaempferol glycosides. Sprague Dawley rats were used to investigate the pharmacokinetic profile of melatonin after oral administration of a lentil sprout extract and to evaluate plasma and urine melatonin and related biomarkers and antioxidant capacity. Melatonin showed maximum concentration (45.4 pg/mL) 90 min after lentil sprout administration. The plasmatic melatonin levels increased after lentil sprout intake (70%, p < 0.05) with respect to the control, 1.2-fold more than after synthetic melatonin ingestion. These increments correlated with urinary 6-sulfatoxymelatonin content (p < 0.05), a key biomarker of plasmatic melatonin. Nonetheless, the phenolic compound content did not exhibit any significant variation. Plasmatic antioxidant status increased in the antioxidant capacity upon both lentil sprout and synthetic melatonin administration. For the first time, we investigated the bioavailability of melatonin from lentil sprouts and its role in plasmatic antioxidant status. We concluded that their intake could increase melatonin plasmatic concentration and attenuate plasmatic oxidative stress.

Exploring Target Genes Involved in the Effect of Quercetin on the Response to Oxidative Stress in Caenorhabditis elegans.

Quercetin is one the most abundant flavonoids in the human diet. Although it is well known that quercetin exhibits a range of biological activities, the mechanisms behind these activities remain unresolved. The aim of this work is to progress in the knowledge of the molecular mechanisms involved in the biological effects of quercetin using Caenorhabditis elegans as a model organism. With this aim, the nematode has been used to explore the ability of this flavonoid to modulate the insulin/insulin-like growth factor 1(IGF-1) signaling pathway (IIS) and the expression of some genes related to stress response. Different methodological approaches have been used, i.e., assays in knockout mutant worms, gene expression assessment by RT-qPCR, and C. elegans transgenic strains expressing green fluorescent protein (GFP) reporters. The results showed that the improvement of the oxidative stress resistance of C. elegans induced by quercetin could be explained, at least in part, by the modulation of the insulin signaling pathway, involving genes age-1, akt-1, akt-2, daf-18, sgk-1, daf-2, and skn-1. However, this effect could be independent of the transcription factors DAF-16 and HSF-1 that regulate this pathway. Moreover, quercetin was also able to increase expression of hsp-16.2 in aged worms. This observation could be of particular interest to explain the effects of enhanced lifespan and greater resistance to stress induced by quercetin in C. elegans, since the expression of many heat shock proteins diminishes in aging worms.

Epicatechin modulates stress-resistance in C. elegans via insulin/IGF-1 signaling pathway.

The nematode Caenorhabditis elegans has been used to examine the influence of epicatechin (EC), an abundant flavonoid in the human diet, in some stress biomarkers (ROS production, lipid peroxidation and protein carbonylation). Furthermore, the ability of EC to modulate the expression of some key genes in the insulin/IGF-1 signaling pathway (IIS), involved in longevity and oxidative or heat shock stress response, has also been explored. The final aim was to contribute to the elucidation of the mechanisms involved in the biological effects of flavonoids. The results showed that EC-treated wild-type C. elegans exhibited increased survival and reduced oxidative damage of biomolecules when submitted to thermal stress. EC treatment led to a moderate elevation in ROS levels, which might activate endogenous mechanisms of defense protecting against oxidative insult. The enhanced stress resistance induced by EC was found to be mediated through the IIS pathway, since assays in daf-2, age-1, akt-1, akt-2, sgk-1, daf-16, skn-1 and hsf-1 loss of function mutant strains failed to show any heat-resistant phenotype against thermal stress when treated with EC. Consistently, EC treatment upregulated the expression of some stress resistance associated genes, such as gst-4, hsp-16.2 and hsp-70, which are downstream regulated by the IIS pathway.

Effect of the addition of mannoproteins on the interaction between wine flavonols and salivary proteins.

It has been suggested that the addition of flavonols (i.e. white grape skins) improves and stabilizes the color of red wines. However, it has been shown that flavonol glycosides produce a mouth-drying and mouth-coating sensation at very low threshold concentrations. Moreover, the addition of polysaccharides to wines is a practice addressed to improve the smoothness and roundness and correct excessive astringency, so we have studied the effect of the addition of yeast mannoproteins (MP) on the interaction between quercetin 3-glucoside and human salivary peptides. Sensory analysis showed the first evidence of the mannoprotein smoothing effect when the flavonol is added to wine. Additionally, MP/SP/polyphenol interactions were studied using fluorescence spectroscopy, dynamic light scattering and isothermal titration calorimetry. Results obtained indicate not only the existence of interactions between mannoproteins and flavonols but also between mannoproteins and salivary proteins (SP), suggesting a possible formation of protein/polyphenol/polysaccharide ternary complex.

Individual contributions of Savinase and Lactobacillus plantarum to lentil functionalization during alkaline pH-controlled fermentation.

Legumes offer the possibility to develop multifunctional foods with benefits for metabolic syndrome. Our objective was to study the effect of alkaline fermentation by Lactobacillus plantarum and Savinase (FLPS) as well the individual effects of both processes on peptides, phenolics and bioactivity of lentil. FLPS increased peptides and some flavonoids and enhanced antioxidant activity, inhibition of angiotensin I-converting enzyme (ACE) and intestinal maltase activities of lentil soluble fraction. Savinase contributed to peptide release, ACE inhibitory and antioxidant activities of lentil soluble fraction. L. plantarum affected to phenolic composition, α-glucosidase and lipase inhibitory activities. Mass spectrometry analysis of the most active fermented lentil subfraction allowed the identification of the main bioactive compounds. Gastrointestinal digestion of fermented lentil increased bioaccessibility of peptides and phenolics as well as antioxidant activity. FLPS enhanced the overall healthy potential of lentil offering the possibility of its use as strategy for lentil functionalization.

Differential effect of quercetin on cisplatin-induced toxicity in kidney and tumor tissues.

Strategies to minimize the nephrotoxicity of platinated antineoplastics without affecting its antitumour efficacy are strongly necessary to improve the pharmacotoxicological profile of these drugs. The natural flavonoid quercetin has been shown to afford nephroprotection without affecting cisplatin antitumour effect. The purpose of the present study has been to assess the differential mechanisms of action of cisplatin and quercetin on kidney and tumour tissues that could explain these effects. Wistar rats bearing subcutaneous tumours were treated with cisplatin and quercetin (and the appropriate controls). Tumour size and renal function evolution was monitored during 6 days. Platinum and quercetin content were also determined in both tissues. All the parameters studied, including blood supply, inflammation, apoptosis, critical MAPK signaling and oxidative stress in the cisplatin-treated animals are almost normalized by quercetin in the kidneys, but unaffected in the tumours. Our results suggest that in a cancer model in vivo, the protection exerted by quercetin on cisplatin nephrotoxicity is related to its antioxidant, vascular, anti-inflammatory and antiapoptotic effects, but these properties do not affect the mechanisms responsible for the antitumour effect of cisplatin.

Betalains and phenolic compounds profiling and antioxidant capacity of pitaya (Stenocereus spp.) fruit from two species (S. Pruinosus and S. stellatus).

Pitaya fruits (Stenocereus spp.) contain betalains and phenolic compounds that have not been completely characterized. Fruits of two ecotypes of S. pruinosus, red-fleshed (SpR) and orange-fleshed (SpO), and two of S. stellatus, red-fleshed (SsR) and white-fleshed (SsW), were characterized in their betalains and phenolic compounds. The chromatographic profile of betalains was similar in SpR, SpO, and SsR, where indicaxanthin, gomphrenin I, phyllocacthin, and their isomers predominated. Betaxanthins content was higher than betacyanins and ranged from 17,706.7±1128.1 to 22,053.6±328.1µg/g dry sample. The identified phenolics mostly corresponded to hydroxycinnamoyl derivatives, flavonols and flavanones. The phenolics content was higher in S. stellatus than in S. pruinosus. The ecotype SsW, that had flesh without color, showed the highest concentration. The antioxidant capacity varied within 9.21±0.84 and 2.41±0.36µmolTrolox/g fresh sample, as determined by the ABTS assay. By its phytochemical composition, the fruits of pitaya can be a good source of antioxidant compounds.

Molecular Approach to the Synergistic Effect on Astringency Elicited by Mixtures of Flavanols.

The interactions between salivary proteins and wine flavanols (catechin, epicatechin, and mixtures thereof) have been studied by HPLC-DAD, isothermal titration microcalorimetry, and molecular dynamics simulations. Chromatographic results suggest that the presence of these flavanol mixtures could facilitate the formation of precipitates to the detriment of soluble aggregates. Comparison between the thermodynamic parameters obtained showed remarkably higher negative values of ΔG in the system containing the mixture of both flavanols in comparison to the systems containing individual flavanols, indicating a more favorable scenario in the mixing system. Also, the apparent binding constants were higher in this system. Furthermore, molecular dynamics simulations suggested a faster and greater cooperative binding of catechin and epicatechin to IB714 peptides when both types of flavanols are present simultaneously in solution.

Flavonoid Composition and Antitumor Activity of Bee Bread Collected in Northeast Portugal.

Bee bread (BB) is a fermented mixture of plant pollen, honey, and bee saliva that worker bees use as food for larvae, and for young bees to produce royal jelly. In the present study, five BB samples, collected from Apis mellifera iberiensis hives located in different apiaries near Bragança, in the northeast region of Portugal, and one BB commercial sample were characterized by high-performance liquid chromatography coupled to a diode array detector and electrospray mass spectrometry (HPLC-DAD-ESI/MS) in terms of phenolic compounds, such as flavonoid glycoside derivatives. Furthermore, the samples were screened, using in vitro assays, against different human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), HeLa (cervical carcinoma) and HepG2 (hepatocellular carcinoma), and also against non-tumor liver cells (porcine liver cells, PLP2). The main phenolic compounds found were flavonol derivatives, mainly quercetin, kaempferol, myricetin, isorhamnetin and herbacetrin glycoside derivatives. Thirty-two compounds were identified in the six BB samples, presenting BB1 and BB3 with the highest contents (6802 and 6480 µg/g extract, respectively) and the highest number of identified compounds. Two isorhamnetin glycoside derivatives, isrohamnetin-O-hexosyl-O-rutinoside and isorhamnetin-O-pentosyl-hexoside, were the most abundant compounds present in BB1; on the other hand, quercetin-3-O-rhamnoside was the most abundant flavonol in BB3. However, it was not possible to establish a correlation between the flavonoids and the observed low to moderate cytotoxicity (ranging from >400 to 68 µg/mL), in which HeLa and NCI-H460 cell lines were the most susceptible to the inhibition. To the authors' knowledge, this is the first report characterizing glycosidic flavonoids in BB samples, contributing to the chemical knowledge of this less explored bee product.

Antioxidant Activity and Phenolic Composition of a Red Bean (Phasoelus vulgaris) Extract and its Fractions.

- The activities of the crude acetonic extract of red bean and its two fractions were determined using a 0-carotene-linoleate model system as well as the total antioxidant activity (TAA), the total phenolics content (TPC), the DPPH radical-scavenging activity, and the reducing power assays. Results from the in vitro assays showed the highest values when tannins (fraction II) were tested. Specifically, the TAA of the tannins fraction was 4.37 mmol Trolox eq./g fraction; whereas, the crude extract and fraction I were 0.481 and 0.093 µmol Trolox eqi/mg extract or fraction, respectively. The content of total phenolics in fraction II was the utmost (612 mg/g); the tannins content, assayed by the vanillin method and expressed as absorbance units at 500 nm per I g, was 938. RP-HPLC- PAD-MS profiling revealed the presence of 33 compounds: quercetin arabinoglucoside, quercetin rutinoside, quercetin, p-hydroxybenzoic acid, and kaempferol rutinoside were the most abundant phenolics in the extract.

Flavonoids as dopaminergic neuromodulators.

SCOPE: The present study aimed to characterize and evaluate flavonoids effects on organic cation uptake in neuronal cells. METHODS AND RESULTS: Uptake experiments were conducted using radiolabeled methyl-4-phenylpyridinuim ([(3) H]-MPP(+) ), in human neuronal dopaminergic cells, SH-SY5Y. Catechin did not alter [(3) H]-MPP(+) uptake, however its metabolite 4'-methyl-catechin decreased it by almost 50%. Epicatechin and its methylated metabolites also decreased [(3) H]-MPP(+) uptake. Interestingly, the quercetin flavonol and its metabolite conjugated with glucuronic acid, as well as the flavanones naringenin and hesperitin, increased [(3) H]-MPP(+) uptake. CONCLUSION: These results showed that different classes of flavonoids, as well as its metabolites, differently influence neuronal organic cation uptake. Several xeno- and endobiotics, including neurotransmitters, are organic cations. Specific food recommendations may be beneficial in pathological conditions where levels of neurotransmitters, as dopamine, are either increased or decreased.

A comparison of the bioactivity and phytochemical profile of three different cultivars of globe amaranth: red, white, and pink.

The phytochemical profiles and bioactivities of red, white and pink globe amaranth (Gomphrena haageana K., Gomphrena globosa var. albiflora and Gomphrena sp., respectively), much less studied than the purple species (G. globosa L.), were compared. The chemical characterization of the samples included the analysis of macronutrients and individual profiles of sugars, organic acids, fatty acids, tocopherols, and phenolic compounds. Their bioactivity was evaluated by determining the antioxidant and anti-inflammatory activities; the absence of cytotoxicity was also determined. Red and pink samples showed the highest sugar content. Otherwise, the white sample gave the highest level of organic acids, and together with the pink one showed the highest tocopherol and PUFA levels. Quercetin-3-O-rutinoside was the major flavonol in white and pink samples, whereas a tetrahydroxy-methylenedioxyflavone was the major compound in the red variety, which revealed a different phenolic profile. The pink globe amaranth hydromethanolic extract revealed the highest antioxidant activity, followed by those of red and white samples. The anti-inflammatory activity was more relevant in red and pink varieties. None of the samples presented toxicity in liver cells. Overall, these samples can be used in bioactive formulations against inflammatory processes and in free radical production.

A survey of modulation of gut microbiota by dietary polyphenols.

Dietary polyphenols present in a broad range of plant foods have been related to beneficial health effects. This review aims to update the current information about the modulation of the gut microbiota by dietary phenolic compounds, from a perspective based on the experimental approaches used. After referring to general aspects of gut microbiota and dietary polyphenols, studies related to this topic are presented according to their experimental design: batch culture fermentations, gastrointestinal simulators, animal model studies, and human intervention studies. In general, studies evidence that dietary polyphenols may contribute to the maintenance of intestinal health by preserving the gut microbial balance through the stimulation of the growth of beneficial bacteria (i.e., lactobacilli and bifidobacteria) and the inhibition of pathogenic bacteria, exerting prebiotic-like effects. Combination of in vitro and in vivo models could help to understand the underlying mechanisms in the polyphenols-microbiota-host triangle and elucidate the implications of polyphenols on human health. From a technological point of view, supplementation with rich-polyphenolic stuffs (phenolic extracts, phenolic-enriched fractions, etc.) could be an effective option to improve health benefits of functional foods such as the case of dairy fermented foods.