Optimizing anthocyanin Oral delivery: Effects of food biomacromolecule types on Nanocarrier performance for enhanced bioavailability.

Wall material types influence the efficacy of nanocarriers in oral delivery systems. We utilized three food biomacromolecules (whey protein isolate, oxidized starch, lipids) to prepare three types of nanocarriers. Our aim was to investigate their performance in digestion, cellular absorption, mucus penetration, intestinal retention, and bioavailability of the encapsulated anthocyanins (Ant). The release rate of protein nanocarriers (Pro-NCs) was twice that of starch nanocarriers (Sta-NCs) and four times that of lipid nanocarriers (Lip-NCs) in simulated gastrointestinal fluid. Additionally, Pro-NCs demonstrated superior transmembrane transport capacity and over three times cellular internalization efficiency than Sta-NCs and Lip-NCs. Sta-NCs exhibited the highest mucus-penetrating capacity, while Pro-NCs displayed the strongest mucoadhesion, resulting in extended gastrointestinal retention time for Pro-NCs. Sta-NCs significantly enhanced the in vivo bioavailability of Ant, nearly twice that of free Ant. Our results demonstrate the critical role of wall material types in optimizing nanocarriers for the specific delivery of bioactive compounds.

Bioavailability of Anthocyanins: Whole Foods versus Extracts.

Anthocyanins have gained significant popularity in recent years for their diverse health benefits, yet their limited bioavailability poses a challenge. To address this concern, technologies have emerged to enhance anthocyanin concentration, often isolating these compounds from other food constituents. However, the extent to which isolated anthocyanins confer health benefits compared to their whole-food counterparts remains unclear. This review explores the current literature on anthocyanin bioavailability and metabolism in the body, with a focus on comparing bioavailability when consumed as extracts versus whole foods rich in anthocyanins, drawing from in vitro, in vivo, and human clinical studies. While direct comparisons between anthocyanin bioavailability in whole foods versus isolates are scarce, prevailing evidence favours whole-food consumption over anthocyanin extracts. Further clinical investigations, preferably with direct comparisons, are needed to validate these findings and elucidate the nuanced interplay between anthocyanins and food matrices, informing future research directions and practical recommendations.

Pharmacokinetic and excretion study of Aronia melanocarpa anthocyanins bound to amylopectin nanoparticles and their main metabolites using high-performance liquid chromatography-tandem mass spectrometry.

Anthocyanins of Aronia melanocarpa are known for their therapeutic properties; however, they are unstable and easily degrade in the environment and in vivo. Herein, we investigated the stability and bioavailability of four anthocyanins bound to amylopectin nanoparticles (APNPs) through a pharmacokinetic and excretion study using high-performance liquid chromatography-tandem mass spectrometry. An EC-C18 column with methanol and 0.1% formic acid as the mobile phase was used during the analysis. After APNP treatment, anthocyanins and metabolites exhibited a marked increase, whereas their maximum oral bioavailability reached 440% and 593%, respectively. The delayed elimination half time demonstrated that APNPs had a sustained-release effect on anthocyanins. Pharmacokinetic results revealed that APNPs effectively protect anthocyanins in vivo. Excretion studies in urine and feces had shown a decrease in excretion of anthocyanins and most of the metabolites after APNP treatment. The results of excretion study further proved the protective effect of APNPs on anthocyanins in vivo.

Bioaccessibility and antioxidant activity of phenolic acids, flavonoids, and anthocyanins of encapsulated Thai rice bran extracts during in vitro gastrointestinal digestion.

Encapsulation technique was applied to improve the stability of bioactive compounds in bran extracts from Thai rice cultivars (Khao Dawk Mali 105, Kiaw Ngu, Hom Nil, and Leum Pua), using three carriers including gelatin, gum Arabic, and the mixture of gelatin and gum Arabic. The microcapsules obtained using gelatin provided a higher production yield of 76.08, 85.63, 85.63 and 85.59%, respectively. A greater encapsulation efficiency was also observed in the extracts encapsulated with gelatin (93.45, 95.91, 91.19 and 95.09%, respectively). After simulated gastric and intestinal digestion, the microcapsules formed by using gelatin exhibited the higher release of bioactive compounds and antioxidant activity than unencapsulated extracts. However, the extracts encapsulated using gelatin and gum Arabic complex yielded the lowest release of bioactive compounds and their antioxidant activity after simulated digestion. The overall results showed that gelatin was an appropriate carrier that could protect bioactive compounds from the digestion conditions.

Effects of Anthocyanin on Intestinal Health: A Systematic Review.

Intestinal health relies on the association between the mucosal immune system, intestinal barrier and gut microbiota. Bioactive components that affect the gut microbiota composition, epithelial physical barrier and intestinal morphology were previously studied. The current systematic review evaluated evidence of anthocyanin effects and the ability to improve gut microbiota composition, their metabolites and parameters of the physical barrier; this was conducted in order to answer the question: "Does food source or extract of anthocyanin promote changes on intestinal parameters?". The data analysis was conducted following the PRISMA guidelines with the search performed at PubMed, Cochrane and Scopus databases for experimental studies, and the risk of bias was assessed by the SYRCLE tool. Twenty-seven studies performed in animal models were included, and evaluated for limitations in heterogeneity, methodologies, absence of information regarding allocation process and investigators' blinding. The data were analyzed, and the anthocyanin supplementation demonstrated positive effects on intestinal health. The main results identified were an increase of Bacteroidetes and a decrease of Firmicutes, an increase of short chain fatty acids production, a decrease of intestinal pH and intestinal permeability, an increase of the number of goblet cells and tight junction proteins and villi improvement in length or height. Thus, the anthocyanin supplementation has a potential effect to improve the intestinal health. PROSPERO (CRD42020204835).

Assembling cyanidin-3-O-glucoside by using low-viscosity alginate to improve its in vitro bioaccessibility and in vivo bioavailability.

In this work, an enteric soluble alginate was proposed to improve the absorption efficiency of cyanidin-3-O-glucoside (C3G) through molecular self-assembly. Under the optimized conditions, the obtained low-viscosity alginate (LVA) was released completely during the simulated gastrointestinal digestion and an LVA-C3G complex with 84.2% binding efficiency was acquired. Fourier transform infrared spectroscopy displayed that the characteristic spectrum of C3G had disappeared after the LVA conjugation. Furthermore, based on the analysis of scanning electron microscopy and differential scanning calorimetry, a porous network structure and the shifted endothermic peak in the thermograms were observed, further confirming the formation of a complex between LVA and C3G. The results of simulated gastrointestinal digestion reveal that the LVA assembly significantly (p < 0.05) improved the bioaccessibility of C3G. Correspondingly, the C3G level in mouse plasma was increased by 27.4% in the C3G-LVA group. This suggests the suitability of LVA as an oral delivery vehicle for dietary anthocyanins.

Metabolic Fate and Cardiometabolic Effects of Phenolic Compounds from Red-Fleshed Apple in Hypercholesterolemic Rats: A Comparative Study with Common White-Fleshed Apple. The AppleCOR Study.

The present study aims to investigate the metabolic fate and the cardiometabolic effects of phenolic compounds provided by a red-fleshed apple variety biofortified in anthocyanins (ACN). Wistar rats are fed with high-fat diet (HFD) to induce hypercholesterolemia and supplemented with red-fleshed apple (HFD+R), white-fleshed apple (HFD+W), or an ACN-rich infusion from aronia fruit (HFD+A) providing matched content and profile of ACN. Plasma biochemical parameters, histological analysis, and phenol biological metabolites are determined. Plasma, urine, and feces show a significant increase of ACN metabolites after HFD+R and HFD+A, while flavan-3-ols are significantly increased after HFD+W and dihydrochalcones derivatives increased after both apples supplementation. A cardioprotective effect is observed after both apples and aronia infusion supplementation in the reduction of aortic thickness. The kidney function is improved after all supplementations and a decrease in insulin plasma concentration after both apples supplementation (HFD+R and HFD+W) is also observed. The findings support that ACN without apple matrix can induce cardioprotective effects. ACN or flavan-3-ols, together with dihydrochalcones, compose a phenolic phytocomplex in red- and white-fleshed apples, respectively, which can act synergistically in the attenuation of cardiovascular outcomes in hypercholesterolemic rats.

Polyphenols and Human Health: The Role of Bioavailability.

Polyphenols are a group of phytochemicals with potential health-promoting effects. They are classified as flavonoid (flavonols, flavanols, flavones, flavanones, isoflavones, and anthocyanins) and non-flavonoid molecules (phenolic acids, hydroxycinnamic acids, lignans, stilbenes, and tannins). Although an increasing number of trials have shown a correlation among polyphenol consumption and a reduction in risk factors for chronic diseases, discrepancies in explaining their positive effects have been found in terms of the bioavailability. In fact, polyphenols show a low bioavailability due to several factors: interaction with the food matrix, the metabolic processes mediated by the liver (phase I and II metabolism), intestine and microbiota. On the other hand, the biological activities of phenol compounds may be mediated by their metabolites, which are produced in vivo, and recent studies have confirmed that these molecules may have antioxidant and anti-phlogistic properties. This review discusses the studies performed in vivo, which consider the polyphenol bioavailability and their different food sources. Factors influencing the biological effects of the main classes of polyphenols are also considered.

Matrix-assisted laser desorption/ionization mass spectrometry-guided visualization analysis of intestinal absorption of acylated anthocyanins in Sprague-Dawley rats.

It is unknown whether intestinal absorption of acylated anthocyanins occurs in their intact or metabolized form. In this study, with the aid of matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) imaging, intestinal absorption of acylated anthocyanins was visually investigated. Anthocyanin extracts from purple carrots were orally administered to Sprague-Dawley rats. Acylated cyanidins were absorbed into portal and circulating blood systems in their intact form, and aglycon; cyanidin 3-O-(6-O-feruloyl-ß-d-glucopyranosyl)-(1 â†’ 6)-[ß-d-xylopyranosyl-(1 â†’ 2)]-ß-d-galactopyranoside (Cy3XFGG), and showed a high absorption of 39.3 ± 0.1 pmol/mL-plasma at 60 min after administration. MALDI-MS imaging analysis of the rat jejunum membranes showed that an organic anion transporting polypeptide (OATP) transporter was involved in Cy3XFGG transport, while deacylated anthocyanins were incorporated through both the glucose transporter 2 and OATP routes. In conclusion, acylated anthocyanin, Cy3XFGG, can be absorbed in its intact form through intestinal OATP.

Improving the physicochemical stability and functionality of nanoliposome using green polymer for the delivery of pelargonidin-3-O-glucoside.

This study aimed to improve the physicochemical stability of nanoliposome (NL) with enhanced functionality for the delivery of Pelargonidin-3-O-glucoside (P3G) using biopolymers, i.e. chitosan (CH) and pectin (P). In this study, we successfully developed stabilized liposomal carriers, i.e. CH-conjugated NL (CH-NL) and P-conjugated CH-NL (P-CH-NL) using an optimum concentration of CH (0.6 wt%) and P (0.5 wt%). Results revealed that P-CH-NL had better physical stability to salt and pH with maximum P3G retention (>97%) under oxidative, thermal, and UV conditions. Nanoliposomes were more stable under refrigerated-storage and ensured high P3G retention (>96%). In vitro mucoadhesion study revealed that CH-NL had better mucin adsorption efficiency (59.72%) followed by P-CH-NL and NL. Furthermore, CH-NL and P-CH-NL alternatively had better stability to serum than NL. Taken together, the stabilization of nanoliposome using chitosan and pectin can be a promising approach for the delivery of hydrophilic compounds in association with enhanced stability and functionality.

Nanocomplexes derived from chitosan and whey protein isolate enhance the thermal stability and slow the release of anthocyanins in simulated digestion and prepared instant coffee.

Anthocyanins (ACNs) are naturally derived colorants and antioxidants added to manufactured foods. ACNs were encapsulated in nanocomplexes with chitosan hydrochloride (CHC), carboxymethyl chitosan (CMC) and whey protein isolate (WPI). The ACN-loaded CHC/CMC-WPI nanocomplexes (ACN-CHC/CMC-WPI) showed a preferred particle size (332.20 nm) and zeta potential (+23.65 mV) and a high encapsulation efficiency (60.70%). ACN-CHC/CMC-WPI nanocomplexes exhibited a smooth spherical shape by transmission electron microscopy. Fourier transform infrared (FT-IR) and Raman spectroscopy confirmed interactions between the ACNs and the encapsulation materials (CHC/CMC-WPI). The nanocomplexes or the nanocomplexes incorporated into coffee beverage better protected ACNs at high temperature compared to the unencapsulated ACNs. In simulated gastrointestinal fluids, the ACNs in the ACN-CHC/CMC-WPI were more stable and more slower released over time. The nanocomplexes maintained high DPPH and hydroxyl free radical scavenging activities. This study indicated that CHC/CMC-WPI nanocomplexes can improve the thermal stability and slow the release of ACNs added to food products.

A network-based pharmacology study of active compounds and targets of Fritillaria thunbergii against influenza.

Seasonal and pandemic influenza infections are serious threats to public health and the global economy. Since antigenic drift reduces the effectiveness of conventional therapies against the virus, herbal medicine has been proposed as an alternative. Fritillaria thunbergii (FT) have been traditionally used to treat airway inflammatory diseases such as coughs, bronchitis, pneumonia, and fever-based illnesses. Herein, we used a network pharmacology-based strategy to predict potential compounds from Fritillaria thunbergii (FT), target genes, and cellular pathways to better combat influenza and influenza-associated diseases. We identified five compounds, and 47 target genes using a compound-target network (C-T). Two compounds (beta-sitosterol and pelargonidin) and nine target genes (BCL2, CASP3, HSP90AA1, ICAM1, JUN, NOS2, PPARG, PTGS1, PTGS2) were identified using a compound-influenza disease target network (C-D). Protein-protein interaction (PPI) network was constructed and we identified eight proteins from nine target genes formed a network. The compound-disease-pathway network (C-D-P) revealed three classes of pathways linked to influenza: cancer, viral diseases, and inflammation. Taken together, our systems biology data from C-T, C-D, PPI and C-D-P networks predicted potent compounds from FT and new therapeutic targets and pathways involved in influenza.

In vitro intestinal transport and anti-inflammatory properties of ideain across Caco-2 transwell model.

The aim of the study was to investigate the absorption and transport mechanisms as well as the anti-inflammatory properties of ideain on Caco-2 transwell model. A concentration and time-dependent bidirectional transport was highlighted; despite this, a clear saturation of the transepithelial absorption in the A-B direction was observed at ideain concentration > 10 µM, suggesting an involvement of membrane transporters. Comparing Papp and PDR values of ideain (10 µM) to reference drugs with a low to a high apparent permeability, it is possible to predict a low in vivo absorption, with a transport efficiency of 1.03%. Co-treatments with several EDTA-Na2 concentrations (1-5 mM) and P-gp inhibition studies with verapamil 100 µM ruled out a passive diffusion of this molecule as well the possibility that P-gp could affect ideain absorption. Inhibition studies using 2 mM phloridzin (SGLT1 inhibitor) and 2 mM phloretin (GLUT2 inhibitor), showed a clear SGLT1 and GLUT2 involvement in the ideain absorption, with SGLT1, which plays the pivotal role. Finally, preliminary anti-inflammatory studies showed that ideain is able to modulate, at a pharmanutritional dose, and with a comparable activity in respect to the reference drug dexamethasone (10 µM), the LPS-induced inflammation in Caco-2 transwell model, which makes it a potentially useful molecule for nutraceutical purpose.

Comparative assessment of phenolic bioaccessibility from 100% grape juice and whole grapes.

Juicing of grapes includes contact with phenolic rich seeds and skins that otherwise rely on maceration for phenolic release. To understand if 100% grape juice can provide a matrix with highly bioaccessible phenolics relative to whole fruit, differences in phenolic content and bioaccessibility from commonly consumed table, Concord (CG) and Niagara (NG) grapes and their 100% juices were compared. Phenolic contents in whole grapes and 100% juices were assayed by LC-MS prior to in vitro digestion to determine phenolic bioaccessibility. Phenolic compounds were concentrated in CG and NG seeds as flavan-3-ols (222.2-285.5 mg per 100 g fw). CG skins were rich in anthocyanins (201.4 mg per 100 g fw) and flavonols (15.5 mg per 100 g fw). Product form had a significant impact on content (p < 0.01), relative bioaccessibility, and absolute bioaccessibility (p < 0.01). CG had a higher total phenolic content (21.9-50.7 mg per 100 g fw) compared to CGJ (5.8 mg per 100 g fw), though NG (4.9-10.8 mg per 100 g fw) was similar in phenolic content to NGJ (9.4-10.8 mg per 100 g fw). Absolute bioaccessibility of total phenolics from CGJ (5.2 mg per 100 g fw) was similar to CG (2.6-9.6 mg per 100 g fw), while NGJ (5.1-5.7 mg per 100 g fw) had higher bioaccessible phenolic content than NG (0.8-1.1 mg per 100 g fw). Differences in bioaccessible content were driven by high relative bioaccessibility of anthocyanins in CGJ (86-135%) compared to CG (14-39%) as well as for flavan-3-ols and phenolic acids from CGJ/NGJ (48-101; 39-85%) compared to CG/NG (0-3; 9-67%). Comparisons between juices and table grapes followed similar trends. A greater fraction of skin and seed phenolics was extracted through juicing and made bioaccessible, making 100% grape juice and whole fruit similar in phenolic delivery to consumers.

Physicochemical stability and in vitro bioaccessibility of phenolic compounds and anthocyanins from Thai rice bran extracts.

The processing and digestive stability of ethanolic extracts from four Thai rice bran varieties, namely Khao Dawk Mali 105, Hom Nil, Kiaw Ngu, and Leum Pua, were assessed by applying different thermal and pH conditions, as well as in vitro gastrointestinal digestion models. High-performance liquid chromatography, Folin-Ciocalteu analysis, as well as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing antioxidant power (FRAP) assays were used to determine the chemical composition, total phenolic content (TPC), and antioxidant activity. Thermal treatment at 100 °C for 15 min induced the degradation of phenolic components and TPC, whereas the antioxidant activities measured by DPPH and FRAP assays remained stable after the heat treatment. Higher phenolic content and antioxidant activity values were observed in the extracts incubated at acidic pH levels of 3 and 5. After simulated digestion, all extracts exhibited the decrease of phenolic compounds and anthocyanin contents, as well as antioxidant activities.

The ameliorating effects of anthocyanins on the cross-linked signaling pathways of cancer dysregulated metabolism.

Cancer cells underlie the dysregulated metabolism of carbohydrate, lipid and protein and thereby, employ interconnected cross-linked signaling pathways to supply adequate energy for growth and related biosynthetic procedures. In the present study, a comprehensive review of cancer metabolism and anthocyanin's effect was conducted using the existing electronic databases, including Medline, PubMed, Scopus, and Web of Science, as well as related articles in the field. Such keywords as "cancer", and "cancer metabolism" in the title/abstract/keyword and all the "anthocyanins" in the whole text were used. Data were collected without time restriction until February 2020. The results indicated the involvement of several signaling pathways, including inflammatory PI3K/Akt/mTOR pathway, Bax/Bcl-2/caspases as apoptosis modulators, and NF-κB/Nrf2 as oxidative stress mediators in the cancer dysregulated metabolism. Compelling studies have shown that targeting these pathways, as critical hallmarks of cancer, plays a critical role in combating cancer dysregulated metabolism. The complexity of cancer metabolism signaling pathways, along with toxicity, high costs, and resistance to conventional drugs urge the need to investigate novel multi-target agents. Increasing evidence has introduced plant-derived secondary metabolites as hopeful anticancer candidates which target multiple dysregulated cross-linked pathways of cancer metabolism. Amongst these metabolites, anthocyanins have demonstrated positive anticancer effects by targeting inflammation, oxidative stress, and apoptotic signaling pathways. The current study revealed the cross-linked signaling pathways of cancer metabolism, as well as the promising pharmacological mechanisms of anthocyanins in targeting the aforementioned signaling mediators. To overcome the pharmacokinetic limitations of anthocyanins in cancer treatment, their interactions with gut microbiota and the need to develop related nano-formulations were also considered.

Colonic delivery of pelargonidin-3-O-glucoside using pectin-chitosan-nanoliposome: Transport mechanism and bioactivity retention.

Colon-targeted delivery is an active area of research as it can improve drug stability, bioactivity, and lessen the systematic toxicity. In this study, the colon-specific delivery of pelargonidin-3-O-glucoside (P3G) was investigated using pectin (P)/chitosan (CH)-functionalized nanoliposome (NL). The food simulant stability, transport mechanism, and bioactivity retention potential of carrier systems were studied. Results showed that polymer-coated nanoliposomes (P-CH-NL and CH-NL) improved the thermal and food simulant stability as well as enhanced the P3G retention during the in vitro digestion. The maximum P3G retention after enzymatic and non-enzymatic digestion was observed by P-CH-NL and the values were 47.5% and 57.5%, respectively. However, all nanoliposomal carriers followed Fickian diffusion mechanism both in in vitro food simulants and in vitro digestion models. Digested functionalized nanoliposomes revealed higher antioxidant properties after gastric digestion. Following by simulated intestinal fluid digestion, ABTS antioxidant activity of P-CH-P3G-NL was 12.52% and 6.31% higher than that of P3G-NL and CH-P3G-NL, respectively, while DPPH scavenging capacity of P-CH-P3G-NL was 5.57% and 1.86% greater than that of P3G-NL and CH-P3G-NL, respectively. Therefore, the developed functionalized nanoliposome can be useful for colon-targeted delivery and applicable in functional foods and/or beverages.

Antioxidant activity and bioaccessibility of phenolic compounds in white, red, blue, purple, yellow and orange edible flowers through a simulated intestinal barrier.

This study assessed the phenolics and their bioaccessibility through an in vitro digestion system coupled to a simulated intestinal barrier in eight edible flowers of distinct colors, namely mini rose, torenia, mini daisy, clitoria, cosmos, cravine, begonia and tagete. The antioxidant activity of the flowers before in vitro digestion, in their derived dialyzed and non-dialyzed fractions was evaluated using distinct approaches. All flowers presented in their composition phenolic acids, stilbenes, flavanol, anthocyanin, flavonol and flavanone, however distinct compounds and contents were found in each flower. The bioaccessibility varied among the phenolics and within the flower source (p < 0.05). Cosmos presented the highest (p < 0.05) content of phenolics and activity in ORAC assay before in vitro digestion and in dialyzed and non-dialyzed fraction; the observed activity was correlated (r = 0.9) to its major compounds, hesperidin and rutin, as well as to caftaric acid and procyanidin B2. Mini rose displayed the highest antioxidant activity in FRAP and DPPH assays before in vitro digestion; its dialyzed and non-dialyzed fraction showed the highest activity in FRAP, correlated to pelargonidin 3,5-diglucoside, catechin, epicatechin galate, epicagocatechin galate, procyanidin A2, quercitin 3-glucoside and trans-resveratrol (r = 0.9). In DPPH assay, mini rose showed the highest activity in the non-dialyzed fraction, while cravine showed the highest activity in the dialyzed fraction, which was mainly correlated to syringic acid (r = 1.0), pelargonidin 3,5-diglucoside and epicatechin (r = 0.9). Results show great variability in the phenolic composition and their bioaccessibility among the edible flowers studied. Our findings indicate cosmos and mini rose as sources of bioaccessible phenolics with great antioxidant activity.

In vitro study of bioaccessibility, antioxidant, and α-glucosidase inhibitory effect of pelargonidin-3-O-glucoside after interacting with beta-lactoglobulin and chitosan/pectin.

Polysaccharides and fruit extracts are applied in dairy products to enhance their nutritional property, but the effects of such formulations on the functions and biological activities are yet to be explored. Therefore, this study was aimed at evaluating the effect of interactions among milk protein (beta-lactoglobulin; BLG), polysaccharides (pectin, P; chitosan, CH), and anthocyanin (pelargonidin-3-O-glucoside; P3G) in improving the bioavailability and biological activity of P3G. After gastrointestinal digestion (GID), the content of free P3G in different model solutions were as follows: P3G-alone (73.59 µg/mL), P3G-P (66.59 µg/mL), P3G-CH (36.72 µg/mL), P3G-BLG (64.92 µg/mL), P3G-P-BLG (64.92 µg/mL), and P3G-CH-BLG (39.61 µg/mL). Less amount of free P3G in model solutions indicated increased complex formation of P3G with protein and/or polysaccharides during GID. These complexes resulted in protection and progressive release of P3G in the gastrointestinal tract. Chitosan exhibited more protection to P3G compared with P and BLG. In addition, α-glucosidase inhibitory activity and ROS scavenging activities of conjugated-P3G samples were potentially augmented after GID. However, the presence of polysaccharides and protein in the model solutions did not show any negative effect on the biological activity of P3G. Thus, pure P3G can be used as a nutritional ingredient in dairy industries.

In vitro gastrointestinal absorption of red wine anthocyanins - Impact of structural complexity and phase II metabolization.

Malvidin-3-O-glucoside, malvidin-3,5-O-diglucoside, malvidin-3-O-(6-O-coumaroyl)-glucoside-5-O-glucoside from Chinese Vitis davidii red wine were used to investigate the role of glucoside, diglucoside and coumaroylated glucoside moieties on their transport efficiency through MKN-28 gastric and Caco-2 intestinal cells. Due to the already described conversion of 3-O-glucosylated anthocyanins into 3-O-glucuronidated, the 3-O-glucuronidated metabolite of malvidin-3-O-glucoside was also tested. The antiproliferative activity was higher for the glucuronidated metabolite in both cell lines. All anthocyanins were transported through MKN-28 gastric cells and Caco-2 intestinal cells with transport efficiencies ranging from 4% to 9% in MKN-28 and from 3% to 5% in Caco-2. No significant differences on transport efficiencies were observed at 180 min among the different anthocyanins in MKN-28. The transport efficiency of malvidin-3-O-glucuronide at 180 min was about 3-4% in Caco-2 and MKN-28 cells. Computational studies were performed to evaluate the interaction between anthocyanins and glucose gastric transporters GLUT1 and GLUT3, which supported the experimental findings.