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Maltodextrin, modified starch, inulin, alginate, gum arabic, and combinations thereof were used as carrier agents for spray drying of carotenoid-rich goldenberry (Physalis peruviana L.) juice and compared to cellobiose as an alternative carrier. Powders were analyzed with respect to particle size and morphology, yield, moisture content, cold water solubility, suspension stability, hygroscopicity, carotenoid encapsulation efficiency, and carotenoid retention during storage. A high initial carotenoid concentration after spray drying, a high encapsulation efficiency of 77.2%, and a slow carotenoid degradation kinetics favored the high carotenoid content of the cellobiose powder at the end of the storage. Cellobiose might protect the carotenoids from degradation processes by light exposure, high temperature, and oxygen due to a tighter particle crust and larger particle sizes. Therefore, cellobiose may be considered a potential carrier agent for the encapsulation of carotenoid-rich fruit juices., Graphical abstract Image 1, Highlights • Goldenberry juice was spray dried with different carrier agents. • Cellobiose was used as carrier agent in the present study for the first time. • The cellobiose powder provided the best retention of carotenoids. • Spray drying promoted isomerization reactions of all-trans-β-carotene. • Cellobiose proved to be effective for spray drying of carotenoid-rich juices.

A pink-coloured bacterium (strain KR32T) was isolated from cheese and assigned to the ‘ Arthrobacter agilis group’. Members of the ‘pink Arthrobacter agilis group’ form a stable clade (100 % bootstrap value) and contain the species Arthrobacter agilis , Arthrobacter ruber and Arthrobacter echini , which share ≥99.0 % 16S rRNA gene sequence similarity. Isolate KR32T showed highest 16S rRNA gene sequence similarity (99.9 %) to A. agilis DSM 20550T. Additional multilocus sequence comparison confirmed the assignment of strain KR32T to the clade ‘pink A. agilis group’. Average nucleotide identity and digital DNA–DNA hybridization values between isolate KR32T and A. agilis DSM 20550T were 82.85 and 26.30 %, respectively. The G+C content of the genomic DNA of isolate KR32T was 69.14 mol%. Chemotaxonomic analysis determined anteiso-C15 : 0 as the predominant fatty acid and MK-9(H2) as the predominant menaquinone. Polar lipids were diphosphatidylglycerol, phosphatidylglycerol, phosphatidylinositol and monoacyldimannosyl-monoacylglycerol. The peptidoglycan type of the isolate was A3α. The carotenoid bacterioruberin was detected as the major pigment. At 10 °C, strain KR32T grew with increased concentrations of bacterioruberin and production of unsaturated fatty acids. Strain KR32T was a Gram-stain-positive, catalase-positive, oxidase-positive and coccus-shaped bacterium with optimal growth at 27–30 °C and pH 8. The results of phylogenetic and phenotypic analyses enabled the differentiation of the isolate from other closely related species of the ‘pink A. agilis group’. Therefore, strain KR32T represents a novel species for which the name Arthrobacter bussei sp. nov. is proposed. The type strain is KR32T (=DSM 109896T=LMG 31480T=NCCB 100733T).

Herein, the antioxidant and food stabilizing properties of a pecan nut shell (PNS) hydroalcoholic extract (PNSE) are reported. Chemical degradation of PNSE demonstrated the presence of condensed tannins as the main phenolic components. PNSE showed remarkable antioxidant properties in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay (EC50 = 0.004 mg/mL). PNSE was initially tested as an inhibitor of mushroom tyrosinase, exhibiting a quite low IC50 value (0.055 mg/mL) against the enzyme diphenolase activity, suggesting its use in enzymatic browning inhibition. The anthocyanin stabilization properties were evaluated under accelerated aging conditions of both pure pigments and commercial fruit juices, and PNSE was found to be effective at concentrations (0.05 mg/mL) at which well-known stabilizers such as chlorogenic and ferulic acids proved to fail. PNSE also performed well in the stabilization of spray-dried anthocyanins for use as a food colorant, increasing the half-life of blackberry anthocyanins up to 20%. In order to explore the possibility of using PNSE as a functional additive for active packaging, polylactic acid (PLA) films containing PNSE were prepared by solvent casting, and no substantial alteration of the mechanical properties was found on addition of the extract up to 10% w/w. The films showed remarkable antioxidant properties (DDPH reduction >60% with a 3% w/w loading, at a dose of 1 mg/mL in the DPPH solution) and delayed the onset of browning of apple smoothies (ca. 30% inhibition with a 10% w/w loading). These results highlight the exploitation of PNS as a low-cost polyphenol source for food industry applications., Pecan nut shell represents an easily accessible and sustainable source of functional additives for food industry applications.

Plant food supplements have experienced increasing popularity and constitute an economically very important group of products. There is a dangerous misperception by many consumers that ‘plant-derived’ means ‘natural’ and ‘safe’. However, various problems are associated with botanicals, including regulatory issues, the complexity of products, interactions with prescription drugs, potential contaminations with natural and anthropogenic toxins, and intentional adulteration, for example, with synthetic pharmaceuticals. Tremendous efforts have been made in the control of the quality and authenticity of botanicals using hyphenated techniques or DNA-based methods. This contribution aims to provide a brief overview of the latest developments in botanicals research, covering the relevant literature mainly between 2015 and 2020. Where appropriate, reference is made also to important papers published earlier.

Polyphenols have attracted huge interest among researchers of various disciplines because of their numerous biological activities, such as antioxidative, antiinflammatory, antiapoptotic, cancer chemopreventive, anticarcinogenic, and antimicrobial properties, and their promising applications in many fields, mainly in the medical, cosmetics, dietary supplement and food industries. In this review, the latest scientific findings in the research on polyphenols interaction with the microbiome and mitochondria, their metabolism and health beneficial effects, their involvement in cognitive diseases and obesity development, as well as some innovations in their analysis, extraction methods, development of cosmetic formulations and functional food are summarized based on the papers presented at the 13th World Congress on Polyphenol Applications. Future implications of polyphenols in disease prevention and their strategic use as prophylactic measures are specifically addressed. Polyphenols may play a key role in our tomorrow´s food and nutrition to prevent many diseases.

Copper in grape musts can influence the fermentation efficiency of Saccharomyces cerevisiae during winemaking. The present study revealed the impact of glutathione addition on yeast strains with va...

The aim of this work was to obtain phase II metabolites of cyanidin-3-O-glucoside and its aglycone using porcine liver enzymes. For this purpose, anthocyanins extracted from blackberry concentrate and containing mostly cyanidin-3-O-glucoside were incubated with the S9, microsomal, and cytosolic fractions of porcine liver. The reactions were targeted to the direction of the respective phase II transformation by the addition of activated cofactors. LC-MSn and LC-IMS-QTOF-MS analyses showed that one methylated, three glucuronidated and three sulfated metabolites of cyanidin-3-O-glucoside were generated. The aglycone, cyanidin, was sulfated and glucuronidated by the liver enzymes. In addition, both were glucuronidated and methylated simultaneously. The detected compounds and the generated data like exact masses, mass spectra, and CCS values may serve as a basis in the search for metabolites formed in vivo. As their effects are largely unexplored, the described synthesis may contribute to a better understandin...

The effects of conventional thermal pasteurization and ultrasound treatment on the peroxidase activity, carotenoid composition, and physicochemical properties (°Brix, pH, and color) of goldenberry (Physalis peruviana L.) puree were investigated in the present study. Response surface methodology was used to determine the optimal process conditions for maximum carotenoid retention and peroxidase inactivation. Complete peroxidase inactivation was achieved only by conventional thermal pasteurization but was associated with losses in total carotenoids of approximately 11.5%. Ultrasonication inactivated peroxidase to a residual activity of 10%, whereas total carotenoids were unaffected within the experimental design. Intensification of the ultrasound process led to higher carotenoid extractability of about 14.7%. Both processing technologies caused changes in the carotenoid profile due to isomerization, deesterification, and further degradation reactions affecting the provitamin A activity. Ultrasound treatment can be suggested as a promising technique to enhance the nutritive value of goldenberry puree.

Psidium fruits are well known in tropical countries as a food and have traditionally been used for the treatment of some diseases, e.g., diarrhea and diabetes. Among them, P. friedrichsthalianum has been associated with positive health effects caused by polyphenols and vitamin C, but detailed information on the phytochemicals involved and their stability during processing is scarce. This study addresses the characterization and quantification of phytochemicals in the peel and flesh of P. friedrichsthalianum using UHPLC-DAD-ESI-MS/MS. Over 100 compounds were characterized, among them proanthocyanidins, ellagitannins, flavanolignans, biflavonoids, and dihydrochalcones. The content of polar secondary metabolites in the peel was approximately 30% higher than in the flesh. B-type proanthocyanidins represented 52.2% and 35.8% in peel and flesh, respectively. During juice processing, geraniin and vescalagin were not affected, whereas other compounds underwent some changes. Castalagin isomers were negatively affected, but pedunculagin isomers, cinnamoyl-O-hexoside, and citric, succinic, and dehydroascorbic acids contents increased. This report highlights the importance of considering Costa Rican guava as a good source of condensed and hydrolysable tannins, i.e., proanthocyanidins and ellagitannins, respectively. Besides, this fruit seems to be a potential raw material for the development of foods, e.g., juice, containing phytochemicals that showed to be stable during pasteurization. Universidad de Costa Rica/[735-A6-912]/UCR/Costa Rica UCR::Vicerrectoría de Investigación::Unidades de Investigación::Ciencias Agroalimentarias::Centro Nacional de Ciencia y Tecnología de Alimentos (CITA)

The effects of traditional pasteurization (low pasteurization, conventional pasteurization, hot filling) and alternative pasteurization (pulsed electric fields, high pressure processing), followed by ultrasonication on the carotenoid content, carotenoid profile, and on the in vitro carotenoid bioaccessibility of orange juice were investigated. There was no significant difference in the total carotenoid content between the untreated juice (879.74 µg/100 g juice) and all pasteurized juices. Significantly lower contents of violaxanthin esters were found in the high thermally-treated juices (conventional pasteurization, hot filling) compared to the untreated juice, owing to heat-induced epoxy-furanoid rearrangement. The additional ultrasonication had almost no effects on the carotenoid content and profile of the orange juices. However, the in vitro solubilization and the micellarization efficiency were strongly increased by ultrasound, the latter by approximately 85.3–159.5%. Therefore, among the applied processing techniques, ultrasonication might be a promising technology to enhance the in vitro bioaccessibility of carotenoids and, thus, the nutritional value of orange juice.

Mineralization of hydrogel biomaterials with calcium phosphate (CaP) is considered advantageous for bone regeneration. Mineralization can be both induced by the enzyme alkaline phosphatase (ALP) and promoted by calcium-binding biomolecules, such as plant-derived polyphenols. In this study, ALP-loaded gellan gum (GG) hydrogels were enriched with gallotannins, a subclass of polyphenols. Five preparations were compared, namely three tannic acids of differing molecular weight (MW), pentagalloyl glucose (PGG), and a gallotannin-rich extract from mango kernel (Mangifera indica L.). Certain gallotannin preparations promoted mineralization to a greater degree than others. The various gallotannin preparations bound differently to ALP and influenced the size of aggregates of ALP, which may be related to ability to promote mineralization. Human osteoblast-like Saos-2 cells grew in eluate from mineralized hydrogels. Gallotannin incorporation impeded cell growth on hydrogels and did not impart antibacterial activity. In conclusion, gallotannin incorporation aided mineralization but reduced cytocompatibility.

Recent in vitro and in vivo studies on anthocyanins confirmed numerous health-promoting effects in humans. Daily anthocyanin intake can be estimated via food databases, but the amount absorbed by the organism still remains uncertain because anthocyanin bioavailability is yet to be elucidated in its entirety. For this purpose, suitable and validated methods of sample preparation and analysis are required. Therefore, a sample preparation method for anthocyanin metabolite analysis in plasma was successfully established and validated. The validation yielded acceptable results for the anthocyanins in terms of recovery (54&ndash, 108%) and precision (coefficient of variation (CV) &lt, 15%). The UHPLC-MS method used in the consecutive reaction monitoring (CRM) mode was sufficiently sensitive, resulting in limits of detection &lt, 2.3 ng/mL and limits of quantification &lt, 8.1 ng/mL with associated repeatability of the MS system with CVs of &lt, 5.1%. In addition, a method for the sum parameter determination of anthocyanidins in urine comprising solely the evaporation of acidified samples was developed, validated, and successfully applied to real samples. The results showed that this method is applicable for the methylated anthocyanidins, but not for the hydroxylated anthocyanidins, due to the chosen CRM modes required for optimum selectivity.

Oxidation of plant phenolics leads to quinones, which are unstable intermediates that may react with nucleophiles. Quinones play an important role in the enzymatic browning of fruits and vegetables and may form covalent adducts with amino acids, peptides, and proteins. These reactions may alter both the physicochemical and immunological properties of food proteins. Quinones trap odoriferous compounds and contribute to the formation of aroma compounds through Strecker degradation of amino acids. Oxidative dimerization of chlorogenic acids in the presence of amino acids leads to the formation of green benzacridines, which are a promising alternative to chlorophylls as food colorants.

Hydroxycinnamic acids are a major group of phenolic compounds widely distributed in plants. Among them, chlorogenic acids and caffeic acid have been in the focus of interest due to their impact on food quality and their putative health benefits. Numerous microorganisms like lactic acid bacteria are able to hydrolyze chlorogenic acids by cinnamoyl esterase enzymes. Data on the specificity of theses enzymes regarding the cleavage of distinct isomers of mono- or dichlorogenic acids is lacking. Lactobacillus reuteri, Lactobacillus helveticus, and Lactobacillus fermentum were screened for their ability to hydrolyze chlorogenic acid isomers in culture medium. Concentrations of chlorogenic acids and the released caffeic acid were determined by UHPLC-ESI-MS. The highest hydrolysis rate (100%) was observed for the hydrolysis of 5-CQA by Lactobacillus helveticus. A so far unknown metabolic pathway for the cleavage of 4-CQA is proposed including isomerization to 5-CQA and 3-CQA followed by hydrolysis.

Carotenoid profiles of goldenberry (Physalis peruviana L.) fruits differing in ripening states and in different fruit fractions (peel, pulp, and calyx of ripe fruits) were investigated by HPLC-DAD-APCI-MSn. Out of the 53 carotenoids detected, 42 were tentatively identified. The carotenoid profile of unripe fruits is dominated by (all-E)-lutein (51%), whereas in ripe fruits, (all-E)-β-carotene (55%) and several carotenoid fatty acid esters, especially lutein esters esterified with myristic and palmitic acid as monoesters or diesters, were found. In overripe fruits, carotenoid conversion products and a higher proportion of carotenoid monoesters to diesters compared to ripe fruits were observed. Overripe fruits showed a significant decrease in total carotenoids of about 31% due to degradation. The observed conversion and degradation processes included epoxidation, isomerization, and deesterification. The peel of ripe goldenberries showed a 2.8 times higher total carotenoid content of 332.00 µg/g dw compared to the pulp.

The iridoid profile of four Vaccinium species was investigated using UHPLC-MS to obtain further information about this group of species for phytochemical characterization. Fruits of bog bilberry (Vaccinium uliginosum L.) showed 14 different iridoid glycosides with a total amount of 20mg/kg fresh weight (FW), whereas bilberry (Vaccinium myrtillus L.) contained 11 iridoid glycosides and a total amount of 127mg/kg FW. Highbush blueberry (Vaccinium corymbosum L.) and lowbush blueberry (Vaccinium angustifolium L.) contained none of the investigated iridoid glycosides. Among the different iridoids, the isomers scandoside and deacetylasperulosidic acid as well as a dihydro derivative thereof were described for the first time in the Ericaceae family. The p-coumaroyl isomers of scandoside, deacetylasperulosidic acid and dihydromonotropein are reported for the first time in V. myrtillus and V. uliginosum. Monotropein and its p-coumaroyl isomers were found for the first time in V. uliginosum. The comparison of iridoid profiles in bilberry fruit and juice samples revealed constant proportions throughout the juice processing. Quantification and profile determination of iridoids may be used for species differentiation and thus for authentication purposes.

Alk(en)ylresorcinols (AR), a class of phenolic lipids, are regarded as antifungal compounds showing high potential for the use in plant protection, especially against Fusarium head blight (FHB). In view of the very limited knowledge of the activity of single AR against Fusarium species, the antifungal effect of crude extracts, fractions and isolated homologues from wheat and rye bran was determined. It was shown that the saturated AR are the active compounds in the extracts, whereas the presence of unsaturated molecules leads to an antagonistic effect. The activity of single saturated AR is dependent on the chain length, but for highest antifungal efficiency a mixture of saturated homologues is required. Affecting the stage of germination, these molecules reduce, and may even completely prevent, the growth of the tested Fusarium species.

Alkylresorcinols (ARs) occur in bran of cereals and in fruits from the Anacardiaceae family. Their separation by liquid chromatography is challenging, especially in rye (Secale cereale L.) that has a complex AR composition. An octyl phase (C8) with 1.8μm particles was used for the analysis of an acetone extract of rye bran. The ARs were detected by UV at 205 and 275nm and by MS applying selected ion monitoring (SIM) of known and hypothetical m/z values in positive and negative mode. The compounds found were subjected to product ion scans in a triple quadrupole mass spectrometer. The C8 UHPLC column has a suitable selectivity for the analysis of ARs from rye. In combination with the sub-2μm particles, baseline separation of most ARs was achieved. The MS2 spectra in positive mode show diagnostic fragments that allow identifying the ARs subclasses (saturated, monoenoic, dienoic, trienoic and hydroxylated monoenoic) unambiguously. Several minor ARs were detected for the first time: C23:3, C27:1OH, C20:0, C22:0, C24:0 and some minor alkenylresorcinol isomers. The chromatographic resolution on the C8 column is unprecedented in the field of rye ARs. Thus, isolation and quantification using non-mass-selective detectors is now possible for each AR. Since rye bran has the most complex AR composition, this method is expected to facilitate the analysis of ARs also in other samples.

The objectives of this work were to determine the phenolic profile of Schinus terebinthifolius and Schinus molle fruits and to develop a reliable method for the differentiation of these two similar spices both known as pink pepper. Anthocyanins, biflavonoids and gallotannins, some of which are reported for the first time in these species, were identified by UHPLC-UV/vis-MS/MS. Consideration of the relative and absolute amounts of phenolics as well as indicator compounds from 18 samples revealed that the relative amounts of anthocyanins and biflavonoids are the most trustworthy parameters. Principal component analysis and cluster analysis (CA) allowed a grouping of the samples according to their species, showing that the anthocyanins are most important for the identification of species. As a result, authentication of the two Schinus species can be accomplished by UHPLC analysis of the relative amounts of anthocyanins combined with CA.

The occasional greening of sweet potatoes and other plant tissues observed during cooking or other food processing has been shown to arise from the autoxidative coupling of chlorogenic,acid (CGA, 5-caffeoylquinic acid) with amino acid components, leading to trihydroxybenzacridine pigments. To explore the potential of this reaction for food coloring, we report herein the optimized biomimetic preparation of trihydroxybenzacridine pigments from CGA and amino acids such as glycine and lysine, their straightforward purification by gel filtration chromatography, the UHPLC-MS/MS analysis of the purified pigment fraction, and a detailed characterization of the pH-dependent trihydroxybenzacridine chromophore. Similar, green pigments were also obtained by analogous reaction of CGA with a low-cost protein, bovine serum albumin, and by simply adding CGA to chicken egg white.(CEW) under stirring. Neither the purified pigments' from amino acids nor the pigmented CEW exerted significant toxicity against two human cell lines, Caco-2 and HepG2, at doses compatible with common use in food coloring. Additions of the pure pigments or pigmented CEW to different food matrices imparted intense green hues, and the thermal stability of these preparations proved satisfactory up to 90 degrees C. The potential application of the greening reaction for the sensing of fish deterioration is also disclosed.

Pigments of pericarp and pulp of pink guava (Psidium guajava L. cv. ‘Criolla’) were investigated to elucidate the profile and the accumulation of main carotenoids during four stages of fruit ripening by using HPLC-DAD and APCI-MS/MS analysis. Seventeen carotenoids were identified, and changes in their profile during fruit ripening were observed. The carotenoids all-trans-β-carotene, 15-cis-lycopene, and all-trans-lycopene were present in all ripening stages, but all-trans-lycopene was found to be predominant (from 63% to 92% of total carotenoids) and responsible for the high lipophilic antioxidant capacity determined by spectrophotometric assays. By using light and transmission electron microscopy, the development of chromoplasts in pericarp and pulp was demonstrated. The accumulation of all-trans-lycopene and all-trans-β-carotene coincided with the development of large crystals; the chromoplasts of pink guava belong, therefore, to the crystalline type. Universidad de Costa Rica/[]/UCR/Costa Rica German Academy Exchange Service/[]/DAAD/Alemania UCR::Vicerrectoría de Investigación::Unidades de Investigación::Ciencias Agroalimentarias::Centro Nacional de Ciencia y Tecnología de Alimentos (CITA) UCR::Vicerrectoría de Docencia::Ciencias Agroalimentarias::Facultad de Ciencias Agroalimentarias::Escuela de Tecnología de Alimentos

Lactating ruminants require an adequate supply of absorbable amino acids for the synthesis of milk protein from two sources, that is crude protein (CP) synthesized microbially in the rumen and ruminally undegraded CP (RUP) from feed which can both be digested in the small intestine. Several chemical and physical methods have been identified as being effective in increasing the proportion of RUP of total CP of a feedstuff, yet there is a continuing need for developing and establishing methods which protect feed protein from ruminal degradation with acceptable expenditure of labour and other costs. The objective of this study was to identify and quantify effects of and interactions between chlorogenic acid and protein in solvent-extracted sunflower meal (SFM) as induced by alkali treatment. Response surface methodology was employed to investigate the influence of pH, reaction time and drying temperature on the resulting SFM and, subsequently, its protein value for ruminants estimated from laboratory values. For this purpose, alkali-treated SFM was subjected to a fractionation of feed CP according to the Cornell net carbohydrate and protein system as a basis for estimating RUP at different assumed ruminal passage rates (Kp ). To estimate the intestinal digestibility of the treated SFM and its RUP, a three-step enzymatic in vitro procedure was applied. Alkaline treatment of SFM increased RUP values with factors ranging from approximately 3 (Kp =.08/hr) to 12 (Kp =.02/hr). Furthermore, the intestinal digestibility of the alkali-treated SFM was enhanced by approximately 10% compared to untreated SFM. Increasing pH and reaction time led to both increasing RUP values and intestinal digestibility. In conclusion, a targeted alkaline treatment of naturally occurring compounds in feedstuffs might be a promising approach to provide high-RUP feeds for ruminants which, at the same time, have improved intestinal digestibility values.

Industrial processing of plant-derived raw materials generates enormous amounts of by-products. On one hand, these by-products constitute a serious disposal issue because they often emerge seasonally and are prone to microbial decay. On the other hand, they are an abundant source of valuable compounds, in particular secondary plant metabolites and cell wall materials, which may be recovered and used to functionalize foods and replace synthetic additives with ingredients of natural origin. This review covers 150 references and presents select studies performed between 2001 and 2016 on the recovery, characterization, and application of valuable constituents from grape pomace, apple pomace, potato peels, tomato pomace, carrot pomace, onion peels, by-products of citrus, mango, banana, and pineapple processing, side streams of olive oil production, and cereal by-products. The criteria used were economic importance, amounts generated, relevance of side streams as a source of valuable compounds, and reviews already published. Despite a plethora of studies carried out on the utilization of side streams, relatively few processes have yet found industrial application.

Anthocyanins or anthocyanin rich extracts from several fruits are frequently applied as food colorants. One major drawback of these natural pigments is their poor stability and the rapid loss of coloring properties. Spray drying of anthocyanin extracts is a suitable approach for encapsulating and stabilizing them. In this study the effects of added copigments (rutin and ferulic acid) on the storage stability of spray-dried anthocyanins from blackberry were investigated. Degradation of anthocyanins during storage under light and different temperatures showed first order kinetics. Light had a higher impact on anthocyanin stability than elevated temperatures. The addition of copigments led to significantly lower anthocyanin losses compared to samples without copigments and to increased half-life values of the obtained powders. This stabilizing effect may be attributed to the antioxidative properties of the copigments and the prevention of the hydration of the anthocyanins. The observed color changes did not correlate with the anthocyanin loss. Degradation of anthocyanin might led to the formation of colored derivatives and polymers during storage.

Flavonoids, synthesized by plants across all families and therefore found in a huge variety, possess a diverse range of pharmacological properties. Direct antibacterial and synergistic activities as well as the inhibition of several bacterial virulence factors are known. Besides the mode of action, it is important to understand the structure-activity relationship to identify key structural characteristics. This study aimed to identify biflavonoids with antibacterial activity from Schinus terebinthifolius Raddi fruits. The purified biflavonoids were characterized in terms of their antibacterial effects. We found that the activity of biflavonoids, including agathisflavone (AGF), amentoflavone (AMF), and tetrahydroamentoflavone (THAF), was dependent on their chemical configuration and degree of oxidation, with THAF showing the highest activity on planktonic cells. Additionally, biofilm formation and composition were strongly influenced by THAF. Even slight differences in the chemical structure have fundamental effects on the activity of isolated biflavonoids. This suggests a specific binding of these substances in bacteria and thus enables detailed investigations of the mode of action in the future.

(1) Background: Polyphenols (PP) play an important role in the prevention of non-communicable diseases and may contribute to healthy aging. To investigate the molecular and cellular aspects of PP metabolites on longevity with a focus on mitochondrial function, we applied a pre-fermented mixture of polyphenols (Rechtsregulat&reg, RR) to rodents and nematodes. (2) Methods: The lifespans of Navar Medical Research Institute (NMRI) mice and C. elegans were recorded. The heat-stress resistance (37 &deg, C) of C. elegans N2 was measured using nucleic staining. Respiration and membrane potential (&Delta, &Psi, m) were measured in isolated mitochondria. The energetic metabolites adenosine triphosphate (ATP), lactate, and pyruvate were determined in lysates. Expression levels of longevity related genes were determined using quantitative real time polymerase chain reaction (qRT-PCR). Phenolic compounds were identified using ultra high performance liquid chromatography-diode array detection-Iontrap-multiple stage mass spectrometry (UHPLC-DAD-Iontrap-MSn). (3) Results: Several phenolic metabolites including protocatechuic acid (PCA) were identified in RR. Feeding of mice with RR resulted in a significantly increased lifespan. Heat-stress resistance (RR *** p = 0.0006, PCA **** p &lt, 0.0001), median lifespan (NMRI: RR ** p = 0.0035, C. elegans RR * p = 0.0279, 0.0001), and activity of mitochondrial respiratory chain complexes (RR *&minus, ** p = 0.0237 &minus, 0.0052, PCA * p = 0.019 &minus, 0.0208) of C. elegans were significantly increased after incubation with RR (10%) or PCA (780 &micro, M). PCA significantly improved nematodes &Delta, m (* p = 0.02058) and ATP levels (* p = 0.029). RR significantly up-regulated lactate levels, indicating enhanced glycolysis. The expression levels of longevity related genes daf-16, sir-2.1, and skn-1 were significantly upregulated after PCA, and partially after RR administration. (4) Conclusion: Phenolic metabolites such as PCA have the potential to enhance health and lifespan and mitochondrial function, and thus may contribute to healthy aging.

Anthocyanins determine the color and potential health-promoting properties of red fruit juices, but the juices contain remarkably less anthocyanins than the fruits, which is partly caused by the interactions of anthocyanins with the residues of cell wall polysaccharides like pectin. In this study, pectin was modified by ultrasound and enzyme treatments to residues of polysaccharides and oligosaccharides widely differing in their molecular weight. Modifications decreased viscosity and degrees of acetylation and methylation and released smooth and hairy region fragments. Native and modified pectin induced different effects on the concentrations of individual anthocyanins after short-term and long-term incubation caused by both hydrophobic and hydrophilic interactions. Results indicate that both pectin and anthocyanin structure influence these interactions. Linear polymers generated by ultrasound formed insoluble anthocyanin complexes, whereas oligosaccharides produced by enzymes formed soluble complexes with protective properties. The structure of the anthocyanin aglycone apparently influenced interactions more than the sugar moiety.

A new sample processing method for analyzing flavonol metabolites in plasma using enzymatic proteolysis was developed and validated. Four endopeptidases were examined regarding their influence on the analyte recovery of quercetin-3- O-glucuronide (Q3GlcA). Methanol was added to inactivate and precipitate the enzymes, and samples were concentrated via evaporation prior to UHPLC-MS analysis. Quercetin-3- O-rutinoside (Q3Rut) was used as an internal standard. The selectivity and accuracy of the established UHPLC-ESI-MS

Berry pomace, rich in polyphenols, especially anthocyanins, accumulates during the production of red juices. Pomace from chokeberry (Aronia melanocarpa Michx.), bilberry (Vaccinium myrtillus L.), and elderberry (Sambucus nigra L.) represent good sources of coloring foodstuffs. Pomace powders (PP) were prepared by milling the seedless fractions of the three dried berry pomaces (50 °C, 8 h). Techno-functional properties of the powders such as particle size distribution, bulk density, sedimentation velocity, and swelling capacity were determined to evaluate the powders for possible food applications. Total anthocyanin content was quantified by UHPLC-DAD before and during a storage experiment to monitor the degradation of anthocyanins in the PP and in a yogurt model application. The high content of phenolic compounds and the still intact cell structure ensured high stability of anthocyanins over 28 days of storage. In the model application, color saturation was stable over the whole storage time of 14 days. Regarding the techno-functional properties, only a few differences between the three PP were observed. The particle size of elderberry PP was larger, resulting in lowest bulk density (0.45 g/mL), high cold-water solubility (16.42%), and a swelling capacity of 10.16 mL/g dw. Sedimentation velocity of the three PP was fast (0.02 mL/min) due to cluster formation of the particles caused by electrostatic and hydrophobic properties. Compared to other high-intensity coloring foodstuffs, the use of PP, showing acceptable color stability with potential health-promoting effects, represents a wide applicability in different food applications and especially in products with a longer shelf-life.

The metabolism of anthocyanins in humans is still not fully understood, which is partly due to the lack of reference compounds. It is known that sulfation is one way of the complex phase II biotransformation mechanism. Therefore, cyanidin-3-O-glucoside and the cyanidin aglycone were chemically converted to their sulfates by reaction with sulfur trioxide-N-triethylamine complex in dimethylformamide. The reaction products were characterized by UHPLC coupled to linear ion trap and IMS-QTOF mass spectrometry. Based on MS data, retention times, and UV-Vis spectra, the compounds could tentatively be assigned to A-, C-, or B-ring sulfates. Analysis of urine samples from two volunteers after ingestion of commercial blackberry nectar demonstrated the presence of two sulfated derivatives of the cyanidin aglycone and one sulfated derivative of the cyanidin-3-O-glucoside. It was found that both the A ring and the B ring are sulfated by human enzymes. This study marks an important step toward a better understanding of anthocyanin metabolism.

Fast methods for the extraction and analysis of various secondary metabolites from cocoa products were developed and optimized regarding speed and separation efficiency. Extraction by pressurized liquid extraction is automated and the extracts are analyzed by rapid reversed-phase ultra high-performance liquid chromatography and normal-phase high-performance liquid chromatography methods. After extraction, no further sample treatment is required before chromatographic analysis. The analytes comprise monomeric and oligomeric flavanols, flavonols, methylxanthins, N-phenylpropenoyl amino acids, and phenolic acids. Polyphenols and N-phenylpropenoyl amino acids are separated in a single run of 33 min, procyanidins are analyzed by normal-phase high-performance liquid chromatography within 16 min, and methylxanthins require only 6 min total run time. A fourth method is suitable for phenolic acids, but only protocatechuic acid was found in relevant quantities. The optimized methods were validated and applied to 27 dark chocolates, one milk chocolate, two cocoa powders and two food supplements based on cocoa extract.

Treatment with cell wall-degrading enzymes is an important step during juice production to enhance juice yield and the amount of value-adding compounds like polyphenols. Enzymatic side activities may lead to unintended alterations of the polyphenol profile. We determined the effects of enzyme treatment on juice yield and content and profile of anthocyanins using four commercial pectinolytic and two cellulolytic enzymes during bilberry juice production. While enzyme dosage at commercial level (0.5 nkat/g) caused only small increases in juice yield but considerably higher anthocyanin yields, significant changes in the anthocyanin profile could be observed, which were related to the glycoside type as well as to the aglycone. Application of excessive enzyme dosage (10 nkat/g) significantly improved both juice yield and total anthocyanin content. Extractability of anthocyanins seems to be more relevant to profile changes during juice processing when usual enzyme dosages are applied, whereas excessive dosages lead to changes caused by enzymatic side activities.

Alkylresorcinols (AR) are a class of phenolic lipids which are found in a number of plants and microorganisms and which are associated with various biological activities. In view of the very limited availability of reference compounds, we developed a process for the isolation of AR from rye bran. For this purpose, a crude extract was subjected to deep bed filtration at -80 °C, whereby the crystallized saturated AR were separated from the unsaturated homologues. Highly purified, individual compounds were subsequently isolated by semi-preparative HPLC. In contrast to previously published approaches, the method reported here is relatively easy to perform and allows the recovery of saturated and unsaturated AR of high purity. Furthermore, it is superior to argentation chromatography because it does not necessitate the removal of silver ions for subsequent bioassays.

The aromatic amino acids and carotenoids are the major contributors to the antioxidant properties of egg yolk. This study aimed to evaluate the effect of simulated retail storage and domestic cooking on the antioxidant activity as well as on the aromatic amino acid and carotenoid contents in ordinary table eggs, omega 3/lutein (n-3/lutein) enriched eggs, and eggs from heritage chicken breeds. The oxygen radical scavenging capacity (ORAC) was the highest in n-3/lutein enriched eggs (161.4μmolTE/gsample), while eggs from heritage white leghorns (HW) showed the lowest levels (127.6μmolTE/gsample). Six weeks of storage at refrigerated temperature did not change the ORAC values, as well as the contents of free amino acid, carotenoid, and malondialdehyde (MDA) in egg yolk. Boiling and frying however, significantly reduced the ORAC value, and the contents of free amino acid, lutein and zeaxanthin, and increased the MDA content in eggs. Our results showed that the antioxidant activity is stable during six weeks of simulated retail storage.

Polyphenols have been associated with various beneficial activities such as antioxidative, antimicrobial or antiproliferative effects. Therefore, they are used as functional ingredients in foods or dietary supplements. Because of the pronounced complexity of this class of compounds, multidisciplinary approaches are needed to characterize these bioactive compounds from food to blood. Understanding polyphenol interactions with other food ingredients like proteins or dietary fiber is of great importance because complex reactions during food processing can take place. Furthermore, these interactions may affect bioaccessibility, as covalently bound polyphenols differ in their food matrix release during absorption in humans. Current research is questioning the accuracy of polyphenol analysis in physiological samples and more studies in this field are required.

Volatile phenols like phenylpropanoid and benzoid compounds originate from the aromatic amino acid phenylalanine, which is biosynthesized via the shikimate/arogenate pathway. These volatile compounds contribute to the aroma of a number of economically important plant-derived foods like herbs, spices and fruits. The sequestration of numerous phenylpropanoid and benzoid compounds as glycosides occurs widely in fruits, and this pool represents an important source of flavor that can be released during storage and processing. Therefore, this review will provide an overview of the biosynthesis of free and glycosylated phenylpropanoid and benzoid compounds and their reactions during food processing, which both lead to the generation of odor-active volatile phenols in plant-derived foods.

The effects of traditional pasteurization (low pasteurization, conventional pasteurization, hot filling) and alternative pasteurization (pulsed electric fields, high pressure processing), followed by ultrasonication on the carotenoid content, carotenoid profile, and on the in vitro carotenoid bioaccessibility of orange juice were investigated. There was no significant difference in the total carotenoid content between the untreated juice (879.74 &micro, g/100 g juice) and all pasteurized juices. Significantly lower contents of violaxanthin esters were found in the high thermally-treated juices (conventional pasteurization, hot filling) compared to the untreated juice, owing to heat-induced epoxy-furanoid rearrangement. The additional ultrasonication had almost no effects on the carotenoid content and profile of the orange juices. However, the in vitro solubilization and the micellarization efficiency were strongly increased by ultrasound, the latter by approximately 85.3&ndash, 159.5%. Therefore, among the applied processing techniques, ultrasonication might be a promising technology to enhance the in vitro bioaccessibility of carotenoids and, thus, the nutritional value of orange juice.

Phenolic compounds are part of the protection system of plants against all kinds of pests and are therefore considered a natural alternative to conventional plant protection agents. Five phenolic compounds (phlorizin, resveratrol, ferulic acid, 5-n-alkylresorcinols, and quercetin) were used as active ingredients in the preparation of a bioactive emulsion and screened for their ability to inhibit the growth of four phytopathogenic fungi - Aspergillus niger, Botrytis cinerea, Penicillium expansum, and Fusarium culmorum. By using design of experiments, several interactions between the phenols were determined, however, ferulic acid was identified as highly effective against the growth of Botrytis cinerea. The growth-inhibitory effect of this emulsion was enhanced by adapting the ferulic acid concentration (0.085%, m/v) with the help of response surface methodology. Subsequent tests confirmed the activity against the growth of nine fungicide-resistant Botrytis cinerea isolates and showed promising results against the infection of injured and contaminated grapes.