Phenolic compounds in Nordic berry species and their application as potential natural food preservatives.

An increasing demand for natural food preservatives is raised by consumers. For Nordic berry species, abundance of phenolic compounds and potent activities of anti-oxidation and anti-bacteria enables a great potential as food preservatives. This review provides a systematic examination of current literature on phenolic profiles, anti-oxidative and anti-bacterial activities of various extracts of Nordic berry species, as well as the impact of various structure features of phenolics on the bioactivities. Special attention is placed on exploitation of leaves of berry species and pomaces after juice-pressing as side-streams of berry production and processing. The current progress and challenges in application of Nordic berry species as food preservatives are discussed. To fully explore the potential application of Nordic berry species in food industry and especially to valorize the side-streams of berry cultivation (leaves) and juice-pressing industry (pomaces), it is crucial to obtain extracts and fractions with targeted phenolic composition, which have high food preserving efficacy and minimal impact on sensory qualities of food products.

Docosahexaenoic acid in regio- and enantiopure triacylglycerols: Oxidative stability and influence of chiral antioxidant.

Docosahexaenoic acid (DHA) is essential for health but easily oxidized. Yet the influence of DHA's exact location (sn-1, sn-2, or sn-3) in triacylglycerols on oxidative stability is currently unknown. This is the first study comparing oxidative stability of DHA in regio- and enantiopure triacylglycerols with or without RRR-α-tocopherol. Headspace solid-phase micro-extraction with gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy were applied. DHA in sn-2 was the most stable with or without added RRR-α-tocopherol resulting in differences in hydroperoxide formation. Without antioxidant, stability of DHA in sn-1 and sn-3 was mainly similar, with slight tendency towards better stability in sn-3. With RRR-α-tocopherol higher stability in sn-1 compared to sn-3 was observed. This points to diastereomeric interactions between RRR-α-tocopherol and DHA in sn-1. These results are highly relevant for enzymatic restructuring processes of DHA-rich fish or microalgae oil concentrates aimed for food supplements or food fortification.

Acupuncture improves the residual urine volume of bladder of middle age patients with urinary retention post-stroke: A protocol for systematic review and meta analysis.

BACKGROUND: There are 15 million new cases of stroke every year in the world, 65% of which have dysuria in the early stage of stroke, which seriously affects the quality of life of stroke patients. The purpose of this study is to evaluate the results of randomized controlled trials to determine whether acupuncture can improve the residual urine volume of the bladder in middle age patients with urinary retention post-stroke. METHODS: Eight databases, including China National Knowledge Infrastructure, Chinese Scientific Journal Database, Cochrane Central Register of Controlled Trials, Embase, MEDLINE, PubMed, Wanfang Database, and Web of Science, will be searched using English and Chinese search strategies. In addition, manual retrieval of research papers, conference papers, ongoing experiments, internal reports, etc, will supplement electronic retrieval. All eligible studies published on or before October 1, 2022 will be selected. To enhance the effectiveness of the study, only clinical randomized controlled trials related to the use of manual acupuncture for the treatment of urinary retention post-stroke will be included. CONCLUSION: The residual urine volume of bladder will be the primary outcome measure, whereas the Clinical efficiency will be the secondary outcomes. Side effects and adverse events will be included as safety evaluations. To ensure the quality of the systematic evaluation, study selection, data extraction, and quality assessment will be independently performed by two authors, whereas a third author will resolve any disagreement.

Effect of Acylated and Nonacylated Anthocyanins on Urine Metabolic Profile during the Development of Type 2 Diabetes in Zucker Diabetic Fatty Rats.

The effect of nonacylated and acylated anthocyanins on urinary metabolites in diabetic rats was investigated. Nonacylated anthocyanins extract from bilberries (NAAB) or acylated anthocyanins extract from purple potatoes (AAPP) was given to Zucker diabetic fatty (ZDF) rats for 8 weeks at daily doses of 25 and 50 mg/kg body weight. 1H NMR metabolomics was applied to study alterations in urinary metabolites from three time points (weeks 1, 4, and 8). Both types of anthocyanins modulated the metabolites associated with the tricarboxylic acid cycle, gut microbiota metabolism, and renal function at weeks 1 and 4, such as 2-oxoglutarate, fumarate, alanine, trigonelline, and hippurate. In addition, only a high dose of AAPP decreased monosaccharides, formate, lactate, and glucose levels at week 4, suggesting improvement in energy production in mitochondria, glucose homeostasis, and oxidative stress. This study suggested different impacts of AAPP and NAAB on the metabolic profile of urine in diabetes.

Similarity Index for the Fat Fraction between Breast Milk and Infant Formulas.

The similarity of the fat fraction in infant formulas rich in either bovine milk fat (MF) or vegetable oil (VO) to breast milk was evaluated by analyzing their lipid composition. Milk fat-rich formulas were highly similar (average similarity index 0.68) to breast milk compared to the VO-rich formulas (average similarity index 0.56). The highest difference in the indices was found in the contents of cholesterol (0.66 vs 0.28 in MF- and VO-rich formulas, respectively, on average) and polar lipids (0.84 vs 0.53), the positional distribution of fatty acids in the sn-2 position of triacylglycerols (0.53 vs 0.28), and fatty acid composition (0.72 vs 0.54). The VO-based formulas were superior in similarity in n - 6 PUFA. Thus, the addition of bovine MF fractions is an effective way to increase the similarity between the lipid composition of infant formulas and human milk.

A novel UHPLC-ESI-MS/MS method and automatic calculation software for regiospecific analysis of triacylglycerols in natural fats and oils.

Regioisomeric analysis of triacylglycerols (TAGs) in natural oils and fats is a highly challenging task in analytical chemistry. Here we present a software (TAG Analyzer) for automatic calculation of regioisomeric composition of TAGs based on the mass spectral data from recently reported ultra-high performance liquid chromatography electrospray ionization tandem mass spectrometry (UHPLC-ESI-MS/MS) method for analyzing TAG regioisomers. The software enables fast and accurate processing of complex product ion spectra containing structurally informative diacylglycerol [M+NH4-RCO2H-NH3]+ and fatty acid ketene [RCO]+ fragment ions. Compared to manual processing, the developed software offers higher throughput with faster calculation as well as more accurate interpretation of chromatographically overlapping isobaric TAGs. The software determines results by constructing a synthetic spectrum to match the measured fragment ion spectrum, and by reporting the optimal concentrations of TAGs used to create the synthetic spectrum. This type of calculation is often extremely challenging for manual interpretation of the fragment ion spectra of isobaric TAGs with shared fragments, hence the need for automated data processing. The developed software was validated by analyzing a wide range of mixtures of regiopure TAG reference compounds of known composition and a commercial olive oil sample. Additionally, the method was also applied for regiospecific analysis of TAGs in human milk as an example of natural fats and oils with a highly complex TAG profile. The results indicate that the software is capable of resolving regioisomeric composition of natural TAGs even of the most complex composition. This novel calculation software combined with our existing UHPLC-ESI-MS/MS method form a highly efficient tool for regioisomeric analysis of TAGs in natural fats and oils.

Impact of enzymatic pre-treatment on composition of nutrients and phytochemicals of canola (Brassica napus) oil press residues.

The study aimed to develop a biorefining process to recover proteins and dietary fibres from a food industry side-stream, canola (Brassica napus) oil pressing residues. The materials were treated with commercial protease, carbohydrase, and phytase to obtain protein-rich supernatants and fibre-rich precipitates. The compositions of these fractions were analyzed using LC-MS (glucosinolates and phenolics) and GC-MS (sugars, acids, and amino acids). Compared to raw material, the supernatants were richer in proteins, sugars, acids, amino acids, phenolic acids, and flavonols; the precipitates had higher levels of minerals and dietary fibres. The enzymatic treatment decreased the contents of phytic acid, glucosinolates, and phenolic alkaloids in all fractions. The applied enzymes effectively enhanced solubility of proteins, despite the lower yield of crude proteins compared to the alkaline extraction (40-82 vs 91 g/100 g dry matters). The impact of enzymes on other chemical components was also revealed by using principal component analysis.

Effects of acylated and nonacylated anthocyanins extracts on gut metabolites and microbiota in diabetic Zucker rats: A metabolomic and metagenomic study.

Anthocyanins have been shown to have prebiotic properties. This study investigated the impact of nonacylated anthocyanins and acylated anthocyanins on fecal and cecal metabolites and colonic gut microbiota in diabetic state using 1H nuclear magnetic resonance (NMR) metabolomics and metagenomic sequencing. Zucker diabetic fatty rats fed with high-fat diet were gavaged with nonacylated anthocyanins extracted from bilberries (NAAB) or acylated anthocyanins extracted from purple potatoes (AAPP) at daily doses of 25 and 50 mg/kg body weight for 8 weeks. Lean Zucker rats fed with normal diet (ND) and high-fat diet (Con) were used as healthy controls groups. Binned NMR spectra and sequenced gene abundance were used for data analysis. Dysbiosis of colonic microbiota and gut metabolites in the diabetic rats were observed compared to the lean Zucker rats. Both anthocyanin extracts increased cecal sugar levels and the abundance of Peptostreptococcaceae sp. and decreased the abundance of Parabacteroides spp. in colon. In addition to the increased fecal short-chain fatty acids, AAPP decreased colonic Ruminococcus torques and Lachnospiraceae bacterium 4_1_37FAA abundances and increased oxidative phosphorylation. The anthocyanin extracts modulated the gut metabolism and microbiota in diabetes, with AAPP showing more regulatory and beneficial effects on diabetes.

Toxicological and bioactivity evaluation of blackcurrant press cake, sea buckthorn leaves and bark from Scots pine and Norway spruce extracts under a green integrated approach.

Aqueous extracts from blackcurrant press cake (BC), Norway spruce bark (NS), Scots pine bark (SP), and sea buckthorn leaves (SB) were obtained using maceration and pressurized hot water and tested for their bioactivities. Maceration provided the extraction of higher dry matter contents, including total phenolics (TPC), anthocyanins, and condensed tannins, which also impacted higher antioxidant activity. NS and SB extracts presented the highest mean values of TPC and antioxidant activity. Individually, NS extract presented high contents of proanthocyanidins, resveratrol, and some phenolic acids. In contrast, SB contained a high concentration of ellagitannins, ellagic acid, and quercetin, explaining the antioxidant activity and antibacterial effects. SP and BC extracts had the lowest TPC and antioxidant activity. However, BC had strong antiviral efficacy, whereas SP can be considered a potential ingredient to inhibit α-amylase. Except for BC, the other extracts decreased reactive oxygen species (ROS) generation in HCT8 and A549 cells. Extracts did not inhibit the production of TNF-alpha in lipopolysaccharide-stimulated THP-1 macrophages but inhibited the ROS generation during the THP-1 cell respiratory burst. The recovery of antioxidant compounds from these by-products is incentivized for high value-added applications.

Phenolic Metabolites in the Urine and Plasma of Healthy Men After Acute Intake of Purple Potato Extract Rich in Methoxysubstituted Monoacylated Anthocyanins.

SCOPE: Structurally stable acylated anthocyanins have potential in various food applications but the effects of acylation and methoxysubstitution on anthocyanin metabolism are poorly understood. This is the first study thoroughly investigating phenolic metabolites, their time-wise changes, and pharmacokinetics following an acute intake of methoxysubstituted monoacylated anthocyanins. METHODS AND RESULTS: Healthy male volunteers (n = 17) consumed a yellow potato meal with and without purple potato extract rich in acylated anthocyanins (152 mg) and hydroxycinnamic acid conjugates (140 mg). Ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) is used for identification and quantification of metabolites from serially collected urine and plasma. While the parent anthocyanins are not detected, 28 phenolic metabolites from urine and 14 from plasma are quantified, including hydroxybenzoic and hydroxycinnamic acids and protocatechuic acid sulfates and glucuronides; three (catechol, gallic acid-4-O-glucuronide, and 2-methoxybenzoic acid) are detected for the first time after anthocyanin-rich food. Urinary hippuric acid is the most abundant with an increase of 139 µM mM-1 creatinine after the treatment. A large additional set of tentatively identified phenolic metabolites are detected. Late urinary peak time values suggest colonic degradation. CONCLUSION: Acylated anthocyanins are more bioavailable than earlier reported after extensive degradation in human and/or colonial metabolism to phenolic metabolites, which may be further conjugated and demethylated.

Red beet (Beta vulgaris) betalains and grape (Vitis vinifera) anthocyanins as colorants in white currant juice - Effect of storage on degradation kinetics, color stability and sensory properties.

Red beet betalains, grape anthocyanins, and their mixtures were used as colorants in white currant juice. Storage stability of the compounds was evaluated using liquid chromatography and the degradation kinetic order and parameters were calculated. Degradation of betalains followed first-order kinetics, while the degradation of anthocyanins did not have any trend toward any order kinetics. The coexisting anthocyanins and their concentration affected the rate constant of betalains. Betalains degraded faster than anthocyanins, their mixtures promoted respective degradation. Pyruvate derivatives of anthocyanins showed better stability. During storage, all samples became more yellowish with CIELab method and lighter in color. In the projective mapping sensory test, samples were distinguished by the colorant type as the main criteria and the storage time as the second criteria. Anthocyanin (described as 'dark' and 'natural') was preferred by sensory panelists over betalain (described as 'pink' and 'unnatural'), as were the fresh samples over stored samples.

Prebiotic Xylo-Oligosaccharides Ameliorate High-Fat-Diet-Induced Hepatic Steatosis in Rats.

Understanding the importance of the gut microbiota (GM) in non-alcoholic fatty liver disease (NAFLD) has raised the hope for therapeutic microbes. We have shown that high hepatic fat content associated with low abundance of Faecalibacterium prausnitzii in humans and, further, the administration of F. prausnitzii prevented NAFLD in mice. Here, we aimed at targeting F. prausnitzii by prebiotic xylo-oligosaccharides (XOS) to treat NAFLD. First, the effect of XOS on F. prausnitzii growth was assessed in vitro. Then, XOS was supplemented or not with high (HFD, 60% of energy from fat) or low (LFD) fat diet for 12 weeks in Wistar rats (n = 10/group). XOS increased F. prausnitzii growth, having only a minor impact on the GM composition. When supplemented with HFD, XOS ameliorated hepatic steatosis. The underlying mechanisms involved enhanced hepatic ß-oxidation and mitochondrial respiration. Nuclear magnetic resonance (1H-NMR) analysis of cecal metabolites showed that, compared to the HFD, the LFD group had a healthier cecal short-chain fatty acid profile and on the HFD, XOS reduced cecal isovalerate and tyrosine, metabolites previously linked to NAFLD. Cecal branched-chain fatty acids associated positively and butyrate negatively with hepatic triglycerides. In conclusion, XOS supplementation can ameliorate NAFLD by improving hepatic oxidative metabolism and affecting GM.

Effects of Anthocyanin Extracts from Bilberry (Vaccinium myrtillus L.) and Purple Potato (Solanum tuberosum L. var. 'Synkeä Sakari') on the Plasma Metabolomic Profile of Zucker Diabetic Fatty Rats.

This study compared the effects of the nonacylated and acylated anthocyanin-rich extracts on plasma metabolic profiles of Zucker diabetic fatty rats. The rats were fed with the nonacylated anthocyanin extract from bilberries (NAAB) or the acylated anthocyanin extract from purple potatoes (AAPP) at daily doses of 25 and 50 mg/kg body weight for 8 weeks. 1H NMR metabolomics was used to study the changes in plasma metabolites. A reduced fasting plasma glucose level was seen in all anthocyanin-fed groups, especially in the groups fed with NAAB. Both NAAB and AAPP decreased the levels of branched-chain amino acids and improved lipid profiles. AAPP increased the glutamine/glutamate ratio and decreased the levels of glycerol and metabolites involved in glycolysis, suggesting improved insulin sensitivity, gluconeogenesis, and glycolysis. AAPP decreased the hepatic TBC1D1 and G6PC messenger RNA level, suggesting regulation of gluconeogenesis and lipogenesis. This study indicated that AAPP and NAAB affected the plasma metabolic profile of diabetic rats differently.

Effect of supercritical CO2 plant extract and berry press cakes on stability and consumer acceptance of frozen Baltic herring (Clupea harengus membras) mince.

A promising way of processing Baltic herring, Clupea harengus membras, is turning the fish into boneless mince. However, Baltic herring is prone to lipid oxidation, which possesses a challenge for industrial applications. The aim of this work was to study the efficacy of press cakes from Finnish berries and a supercritical CO2 plant extract to limit lipid oxidation during frozen storage of Baltic herring mince and to determine the impact of these additions on consumer acceptance in a fish product. Peroxide value, formation of volatile oxidation products and loss of polyunsaturated fatty acids showed that the tested natural additives decreased oxidation to a greater or similar extent as conventional antioxidants during 10-month storage. While potential of berry press cakes and plant extracts as "green label antioxidants" was shown, consumer study indicated need for further research to reach both optimal antioxidative efficacy and sensory properties.

Characterization and Quantification of Nonanthocyanin Phenolic Compounds in White and Blue Bilberry (Vaccinium myrtillus) Juices and Wines Using UHPLC-DAD-ESI-QTOF-MS and UHPLC-DAD.

The nonanthocyanin phenolic compounds in juice and wine produced from fruits of white bilberry, a nonpigmented mutant of Vaccinium myrtillus, and blue bilberry (pigmented variety) were analyzed using liquid chromatography with a diode array detector (LC-DAD) and LC-DAD-electrospray ionization-quadrapole/time of flight hybrid mass spectrometry (ESI-QTOF-MS). On the basis of elution order, UV-vis spectra, accurate mass data, and fragmentation pattern and standards, 42 compounds including 22 phenolic acids, 15 flavonols, and 5 flavan-3-ols, were identified in juices and wines prepared from the two bilberry varieties. The levels of most individual nonanthocyanin phenolic compounds in white bilberry products were significantly lower than those in pigmented ones. In bilberry juices, phenolic acids were the most predominant, accounting for approximately 80% of total phenolic content, with p-coumaroyl monotropeins and caffeic acid hexoside being the major phenolic acids. After fermentation, the total contents of phenolic acids, flavonols, and nonanthocyanin phenolic compounds significantly increased, while the content of total flavan-3-ols decreased significantly. p-Coumaroyl monotropeins still dominated in the wine products, while caffeic acid content showed dramatic elevation with the significant drop of caffeic acid hexoside.

Impact of cultivar, growth temperature and developmental stage on phenolic compounds and ascorbic acid in purple and yellow potato tubers.

Phenolic compounds and ascorbic acid were analyzed in one yellow and four purple-flesh potato cultivars grown at 13 °C and 18 °C and harvested at different stages of tuber development, using HPLC-DAD and UHPLC-MS. The expression of genes in the phenylpropanoid pathway was studied at transcription level using qPCR. Petunidin-3-p-coumaroylrutinoside-5-glucoside was the most abundant anthocyanin in 'Blue Congo', 'Blaue Schweden', and 'Synkeä Sakari', whereas malvidin-3-p-coumaroylrutinoside-5-glucoside dominated in 'Blaue Veltlin'. In mature tubers, the purple cultivar 'Synkeä Sakari' showed the highest content of anthocyanins (2.4 mg/g freeze-dried sample), and 'Blaue Veltlin' had the highest content of phenolic acids (5.5 mg/g). Cultivar was the main variable affecting the biosynthesis of the studied metabolites, whereas the temperatures studied did not show different impact. The content of the main phenolic acids and anthocyanins in the potato cultivars correlated positively with the expression levels of the genes involved in the phenylpropanoid pathway.

Hops compounds modulatory effects and 6-prenylnaringenin dual mode of action on GABAA receptors.

Hops (Humulus lupulus L.), a major component of beer, contain potentially neuroactive compounds that made it useful in traditional medicine as a sleeping aid. The present study aims to investigate the individual components in hops acting as allosteric modulators in GABAA receptors and bring further insight into the mode of action behind the sedative properties of hops. GABA-potentiating effects were measured using [3H]ethynylbicycloorthobenzoate (EBOB) radioligand binding assay in native GABAA receptors. Flumazenil sensitivity of GABA-potentiating effects, [3H]Ro 15-4513, and [3H]flunitrazepam binding assays were used to examine the binding to the classical benzodiazepines site. Humulone (alpha acid) and 6-prenylnaringenin (prenylflavonoid) were the most potent compounds displaying a modulatory activity at low micromolar concentrations. Humulone and 6-prenylnaringenin potentiated GABA-induced displacement of [3H]EBOB binding in a concentration-dependent manner where the IC50 values for this potentiation in native GABAA receptors were 3.2 µM and 3.7 µM, respectively. Flumazenil had no significant effects on humulone- or 6-prenylnaringenin-induced displacement of [3H]EBOB binding. [3H]Ro 15-4513 and [3H]flunitrazepam displacements were only minor with humulone but surprisingly prominent with 6-prenylnaringenin despite its flumazenil-insensitive modulatory activity. Thus, we applied molecular docking methods to investigate putative binding sites and poses of 6-prenylnaringenin at the GABAA receptor α1ß2γ2 isoform. Radioligand binding and docking results suggest a dual mode of action by 6-prenylnaringenin on GABAA receptors where it may act as a positive allosteric modulator at α+ß- binding interface as well as a null modulator at the flumazenil-sensitive α+γ2- binding interface.

Anthocyanin-rich extract from purple potatoes decreases postprandial glycemic response and affects inflammation markers in healthy men.

Our recent clinical study suggested that polyphenol-rich purple potatoes lowered postprandial glycemia and insulinemia compared to yellow potatoes. Here, 17 healthy male volunteers consumed yellow potatoes with or without purple potato extract (PPE, extracted with water/ethanol/acetic acid) rich in acylated anthocyanins (152 mg) and other phenolics (140 mg) in a randomized cross-over trial. Ethanol-free PPE decreased the incremental area under the curve for glucose (p = 0.019) and insulin (p = 0.015) until 120 min after the meal, glucose at 20 min (p = 0.015) and 40 min (p = 0.004), and insulin at 20 min (p = 0.003), 40 min (p = 0.004) and 60 min (p = 0.005) after the meal. PPE affected some of the studied 90 inflammation markers after meal; for example insulin-like hormone FGF-19 levels were elevated at 240 min (p = 0.001). These results indicate that PPE alleviates postprandial glycemia and insulinemia, and affects postprandial inflammation.

Effects of Latitude and Weather Conditions on Proanthocyanidins in Blackcurrant (Ribes nigrum) of Finnish Commercial Cultivars.

Blackcurrants of three Finnish commercial cultivars 'Mortti', 'Ola', and 'Melalahti' cultivated in southern and northern Finland were compared on the basis of the content and composition of proanthocyanidins (PAs). Seventeen B-type PA oligomers (degree of polymerization 2-5 and 7) were detected by hydrophilic interaction liquid chromatography and electrospray ionization mass spectrometry. Total PAs, dimers, trimers, and tetramers were quantified. Among the three cultivars, 'Ola' had the highest contents of both total PAs and PA oligomers. 'Melalahti' was separated from both 'Mortti' and 'Ola' by PA profiles in the partial least-squares discriminant analysis model. All three cultivars revealed distinct responses to latitude and weather conditions. The content of total PAs showed a positive correlation to latitude in 'Ola' and 'Melalahti'. Among the meteorological variables, high temperature and radiation correlated negatively with total PAs, while only specific variables showed a correlation with PA oligomers.

Changes in the volatile profile, fatty acid composition and other markers of lipid oxidation of six different vegetable oils during short-term deep-frying.

Oil deterioration during deep-frying influences the quality of fried foods to a great extent. In this study, the frying performance of six vegetable oils, i.e., hemp, lupin, oat, rapeseed, soy, and sunflower, was evaluated following short-term (60 min) deep-frying of French fries at 180 °C. The frying oils were investigated for fatty acid profile, volatile compound composition, and parameters of oxidative stability, such as iodine, peroxide, and p-anisidine values. The examination showed that the content of Æ©PUFA in hemp oil decreased significantly (p < 0.05) after 60 min of deep-frying, although the degree of change was relatively small (close to 1.5%). Similarly, soy oil presented a fatty acid profile prone to oxidation, and generated the highest level of peroxides at the end of the thermal treatment (PV = 16.6 ±â€¯2.3 mEq O2 kg-1). As for the volatile compound composition of the oils, sunflower oil was extensively affected by the deep-frying treatment with a significant decrease (p > 0.05) in total terpenes, accompanied by a considerable rise in total aldehydes. Oppositely, the proportions of MUFA and PUFA of lupin and oat oils remained stable (p > 0.05) during the short-term deep-frying, indicating high stability of these oils. The research provided new data for evaluating the suitability of these oils for household food preparations.