The presented work describes the development and validation of a rapid UHPLC-UV method using a core-shell particle column with a pentafluorophenyl stationary phase for the separation and quantitative analysis of the six anthocyanins in acai berry and dry blueberry extracts. The anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutenoside, delphinidin-3-galactoside, delphinidin-3-glucoside, delphinidin-3-rutenoside, and peonidin-3-glucoside) were separated and analyzed in 5min. The chromatographic separation was performed on a Kinetex PFP (150×2.1mm) core-shell column with a particle size of 1.7μm at a temperature of 50°C. Acetonitrile was used as mobile phase B and 5% formic acid, filtrated through a 0.22μm filter, as mobile phase A. They were delivered at a flow rate of 0.55mLmin-1 according to the elution gradient program. The detection wavelength was set at 520nm. A solid-liquid extraction with a solution of methanol and a 5% water solution of formic acid (25+75v/v) using an ultrasonic bath was chosen for the preparation of the available commercial samples of food supplements with a content of acai berry extract and blueberry extract. Under optimal chromatographic conditions, the method was validated. Recoveries for all analyzed anthocyanins were 97.8-102.6% and the relative standard deviation ranged from 0.4% to 3.0% for within-day and from 0.6% to 3.1% for between-day repeatability. The limits of detection were in the range of 0.11-0.14μgmL-1.

• Klíčová slova
• Acai berry, Anthocyanins, Blueberry, Core-shell column, Fast separation, Plant extracts,
• MeSH
• anthokyaniny MeSH
• Euterpe * MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• anthokyaniny MeSH

Desorption electrospray ionization (DESI) mass spectrometry appears to be a useful technique applicable in different areas (e.g. analysis of pharmaceuticals, identification of biologically active compounds in tissues, imaging mass spectrometry). Its modification termed desorption nano-electrospray (nano-DESI) was tested for analysis of anthocyanins. Acidifying of samples and acidic spray liquid (methanol:water=75:25 with 0.2% HCOOH) were essential for obtaining good quality spectra. Profiles of main anthocyanins in wine samples, two vintages (2005 and 2007) of three cultivars (Alibernet, Neronet and Rubinet), were successfully acquired. They were in agreement with results of LC/MS experiments (anthocyanins isolated by solid phase extraction were separated by mu-HPLC with gradient elution and detected by ESI-MS). Nano-DESI-MS data also allowed to determine ratio of two cultivars (Neronet and Rubinet) in their mixture and to detect coloring of wine by tenturier or elderberry extract. Detection of main anthocyanins in slices of wine grape, chokeberries and elderberries or in a wine stain on cotton fabric is also presented.

• MeSH
• anthokyaniny analýza   MeSH
• hmotnostní spektrometrie s elektrosprejovou ionizací metody   MeSH
• řízení kvality MeSH
• víno analýza   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• anthokyaniny MeSH

A high-performance liquid chromatography method using an alternative pentafluorophenyl (PFP) core-shell stationary phase has been developed and used for rapid separation of 23 anthocyanins in a highbush blueberry Bluehaven cultivar. A high efficiency of separation of anthocyanins was achieved in the core-shell column Kinetex PFP, 150×4.6mm (particle size 2.6µm) with a 5×4.6mm precolumn, using a simple linear gradient elution with a mobile phase of acetonitrile and a water solution of 2% formic acid at a flow rate of 1.0ml/min and at a temperature of 50°C. The detection wavelength was set at 520nm for detection of all anthocyanins. The homogenized blueberry sample (Bluehaven cultivar) was extracted using pure methanol with 1.3% formic acid using an ultrasound bath for 20min and then filtrated. A 5-µL sample volume was directly injected into the HPLC system. The developed method showed an efficient separation of 23 anthocyanins in a total runtime of 21min. The potential of the pentafluorophenyl phase for efficient separation was demonstrated on a wide range of anthocyanins varying in glycosylation and acylation patterns found in highbush blueberries. The fluorinated stationary phase showed an alternative and complementary separation approach providing unique aromatic and polar selectivity in comparison with common C-18 phases.

• Klíčová slova
• Anthocyanins, Blueberry, Chromatography, Core-shell columns, Pentafluorophenyl (PFP), Separation,
• MeSH
• anthokyaniny analýza   izolace a purifikace   MeSH
• brusnice s jedlými plody chemie   MeSH
• časové faktory MeSH
• halogenace MeSH
• vysokoúčinná kapalinová chromatografie metody   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• anthokyaniny MeSH

Anthocyanins are generally considered to be the largest and the most important group of water-soluble pigments in plants. They are widely consumed by humans as natural compounds of vegetables, fruits, and red wine. Anthocyanins as well as other flavonoids show protective qualities against variety of pathologies, including cardiovascular diseases, cancer, diabetes mellitus, neurodegeneration, inflammation, viral infections, and obesity. Many healthy properties of anthocyanins are related to their antioxidant potency. Broad evidence of beneficial effects of anthocyanins on human health has led to their increasing popularity in the form of food supplements and nutraceuticals. As the nutraceuticals contain concentrated bioactive agents, consumed doses exceed those that could be obtained from food. Therefore, apart from anticipated improvement of human health it is essential to have in mind possible unexpected effects of anthocyanins. Interaction of these compounds with drug-metabolizing enzymes and transporters may affect the fate of co-administered drugs and thus exert pharmacological consequences. On the other hand, the modulation of certain drug-metabolizing and antioxidant enzymes by anthocyanins can contribute to chemoprotection and antioxidant defense of organisms. The present review summarizes anthocyanin properties with emphasis on the antioxidant capacity and deals with the potential of anthocyanins to modulate phase I and II drug-metabolizing enzymes, transporters and antioxidant enzymes. The undesirable and/or beneficial outcomes of possible interactions of anthocyanins with drugs or industrial pollutants are also discussed.

• MeSH
• anthokyaniny chemie   metabolismus   terapeutické užití   MeSH
• léčivé přípravky metabolismus   MeSH
• lékové interakce MeSH
• lidé MeSH
• nádory farmakoterapie   prevence a kontrola   MeSH
• oxidoreduktasy chemie   metabolismus   MeSH
• systém (enzymů) cytochromů P-450 metabolismus   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• přehledy MeSH
• Názvy látek
• anthokyaniny MeSH
• léčivé přípravky MeSH
• oxidoreduktasy MeSH
• systém (enzymů) cytochromů P-450 MeSH

The octanol-water partition coefficients of seven anthocyanins (in neutral form, pH = 7.0) were measured by means of MEKC. A new iterative method for the estimation of migration time of electroosmotic flow (EOF) and micelles in MEKC is presented. This calculation is based on Gauss-Newton linearization of the dependence between migration indices and migration times of a set of suitable standards and the application of an advanced statistical evaluation procedure. The values of partition coefficients obtained with the aid of an iterative process are compared with values obtained on use of EOF and micelle markers.

• MeSH
• anthokyaniny chemie   izolace a purifikace   MeSH
• chromatografie micelární elektrokinetická kapilární metody   statistika a číselné údaje   MeSH
• hydrofobní a hydrofilní interakce MeSH
• koncentrace vodíkových iontů MeSH
• micely MeSH
• oktanoly MeSH
• statistické modely MeSH
• voda MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• anthokyaniny MeSH
• micely MeSH
• oktanoly MeSH
• voda MeSH

OBJECTIVES: The aim of this work was to assess the possible beneficial effects of aqueous extracts of Hibiscus sabdariffa L. calyces and anthocyanins isolated therefrom in an adenine-induced chronic kidney disease (CKD) model. METHODS: Rats were orally given, for 28 consecutive days, either adenine alone or together with either aqueous extract of H. sabdariffa calyces (5 and 10%) or anthocyanins (50, 100 and 200 mg/kg of anthocyanin concentrate). For comparative purposes, two groups of rats were given lisinopril (10 mg/kg). KEY FINDINGS: When either H. sabdariffa aqueous extract or the anthocyanins isolated from it was administered along with adenine, the adverse effects of adenine-induced CKD were significantly lessened, mostly in a dose-dependent manner. The positive effects were similar to those obtained by administration of lisinopril. CONCLUSIONS: The results obtained show that both H. sabdariffa and its anthocyanins could be considered as possible promising safe dietary agents that could be used to attenuate the progression of human CKD. This could have added significance as H. sabdariffa tea is widely consumed in many parts of Africa and Asia and is thus readily available.

• Klíčová slova
• Hibiscus sabdariffa, adenine, anthocyanins, chronic kidney disease, rats,
• MeSH
• adenin toxicita   MeSH
• anthokyaniny aplikace a dávkování   izolace a purifikace   farmakologie   MeSH
• aplikace orální MeSH
• chronická renální insuficience farmakoterapie   patofyziologie   MeSH
• Hibiscus chemie   MeSH
• krysa rodu Rattus MeSH
• lisinopril farmakologie   MeSH
• modely nemocí na zvířatech MeSH
• potkani Wistar MeSH
• rostlinné extrakty aplikace a dávkování   farmakologie   MeSH
• vztah mezi dávkou a účinkem léčiva MeSH
• zvířata MeSH
• Check Tag
• krysa rodu Rattus MeSH
• mužské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• srovnávací studie MeSH
• Názvy látek
• adenin MeSH
• anthokyaniny MeSH
• lisinopril MeSH
• rostlinné extrakty MeSH

Besides signalling to soil organisms, strigolactones (SLs) control above- and below-ground morphology, in particular shoot branching. Furthermore, SLs interact with stress responses, possibly thanks to a crosstalk with the abscisic acid (ABA) signal. In grapevine (Vitis vinifera L.), ABA drives the accumulation of anthocyanins over the ripening season. In this study, we investigated the effects of treatment with a synthetic strigolactone analogue, GR24, on anthocyanin accumulation in grape berries, in the presence or absence of exogenous ABA treatment. Experiments were performed both on severed, incubated berries, and on berries attached to the vine. Furthermore, we analysed the corresponding transcript concentrations of genes involved in anthocyanin biosynthesis, and in ABA biosynthesis, metabolism, and membrane transport. During the experiment time courses, berries showed the expected increase in soluble sugars and anthocyanins. GR24 treatment had no or little effect on anthocyanin accumulation, or on gene expression levels. Exogenous ABA treatment activated soluble sugar and anthocyanin accumulation, and enhanced expression of anthocyanin and ABA biosynthetic genes, and that of genes involved in ABA hydroxylation and membrane transport. Co-treatment of GR24 with ABA delayed anthocyanin accumulation, decreased expression of anthocyanin biosynthetic genes, and negatively affected ABA concentration. GR24 also enhanced the ABA-induced activation of ABA hydroxylase genes, while it down-regulated the ABA-induced activation of ABA transport genes. Our results show that GR24 affects the ABA-induced activation of anthocyanin biosynthesis in this non-climacteric fruit. We discuss possible mechanisms underlying this effect, and the potential role of SLs in ripening of non-ABA-treated berries.

• MeSH
• anthokyaniny metabolismus   MeSH
• kyselina abscisová metabolismus   MeSH
• laktony farmakologie   MeSH
• ovoce účinky léků   metabolismus   MeSH
• regulátory růstu rostlin metabolismus   farmakologie   MeSH
• Vitis účinky léků   metabolismus   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• anthokyaniny MeSH
• kyselina abscisová MeSH
• laktony MeSH
• regulátory růstu rostlin MeSH

Degradation of anthocyanins involves scission of the flavonoid skeleton yielding 2,4,6-trihydroxybenzaldehyde (phloroglucinaldehyde, PGA) and a phenolic acid. However, the process is not finished with the formation of PGA, as the consequent condensation of two PGA molecules providing colored hydroxylated anthraquinones was observed for the first time. This process was studied using a combination of preparative column chromatography, nuclear magnetic resonance, liquid chromatography/high resolution tandem mass spectrometry (LC/HRMS2), and quantum calculations using density functional theory. 1,3,5,7-tetrahydroxyanthraquinone (anthrachrysone) and its isomers were found to rise during heating (95 °C) in a buffered PGA model solution (phosphate buffer, pH 7). These compounds were detected in heated red wine after an increase of its pH value. The concentration of the identified anthrachrysone in the red wine reached 0.01 mg·L-1. Presence of those compounds could therefore indicate involvement of certain steps in the processing of plant materials rich in anthocyanins (e.g., utilization of a higher temperature and/or reduction of acidity) or long-term transformation of anthocyanins (potentially, for instance, in archaeological findings such as wine or fruit residues). Additionally, measurement of wine-soil suspensions proved an increase of their pH to the values suitable for anthocyanin cleavage (neutral to slightly alkaline; reached using soil from archaeologically well-known Bull Rock Cave). Although not found in artificially prepared samples (imitations) or authentic materials so far, according to our results the above mentioned conditions are suitable for the formation of tetrahydroxylated anthraquinone derivatives and their monitoring would be beneficial.

• Klíčová slova
• anthocyanin, degradation, hydroxyanthraquinone, phloroglucinaldehyde, wine,
• MeSH
• analýza potravin * metody   MeSH
• anthokyaniny chemie   MeSH
• anthrachinony analýza   chemie   MeSH
• chromatografie kapalinová MeSH
• hmotnostní spektrometrie MeSH
• molekulární modely MeSH
• molekulární struktura MeSH
• víno analýza   MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• anthokyaniny MeSH
• anthrachinony MeSH

Anthocyanins are plant pigments occurring in flowers and berry fruits. Since a phenomenon of food-drug interactions is increasingly emerging, we examined the effects of 21 major anthocyanins and the extracts from 3 food supplements containing anthocyanins on the aryl hydrocarbon receptor (AhR)-cytochrome P450 CYP1A1 signaling pathway in human hepatocytes and human hepatic HepG2 and intestinal LS174T cancer cells. Pelargonidin-3-O-rutinoside (PEL-2) and cyanidin-3,5-O-diglucoside (CYA-3) dose-dependently activated AhR, as revealed by gene reporter assay. PEL-2 and CYA-3 induced CYP1A1 mRNA but not protein in HepG2 and LS174T cells. Neither compounds induced CYP1A1 mRNA and protein in four different primary human hepatocytes cultures. The effects of PEL-2 and CYA-3 on AhR occurred by ligand-dependent and ligand-independent mechanisms, respectively, as demonstrated by ligand binding assay. In a direct enzyme inhibition assay, none of the antocyanins tested inhibited the CYP1A1 marker activity to less than 50% even at 100 μM concentration. PEL-2 and CYA-3 at 100 μM inhibited CYP1A1 to 79% and 65%, respectively. In conclusion, with exception of PEL-2 and CYA-3, there were no effects of 19 major anthocyanins and 3 food supplements containing anthocyanins on AhR-CYP1A1 signaling, implying zero potential of these compounds for food-drug interactions with respect to AhR-CYP1A1 pathway.

• Klíčová slova
• 2,3,7,8-tetrachlorodibenzo-p-dioxin, AhR, Anthocyanins, Aryl hydrocarbon receptor, Cytochrome P450, Food supplements, Food–drug interactions, TCDD, aryl hydrocarbon receptor,
• MeSH
• anthokyaniny chemie   toxicita   MeSH
• buňky Hep G2 MeSH
• cytochrom P-450 CYP1A1 metabolismus   MeSH
• dospělí MeSH
• glukosidy chemie   toxicita   MeSH
• hepatocyty účinky léků   metabolismus   MeSH
• inhibitory enzymů toxicita   MeSH
• interakce mezi potravou a léky MeSH
• jaterní mikrozomy účinky léků   enzymologie   MeSH
• lidé středního věku MeSH
• lidé MeSH
• potravní doplňky MeSH
• receptory aromatických uhlovodíků účinky léků   metabolismus   MeSH
• regulace genové exprese enzymů účinky léků   MeSH
• signální transdukce účinky léků   MeSH
• vazba proteinů MeSH
• viabilita buněk účinky léků   MeSH
• Check Tag
• dospělí MeSH
• lidé středního věku MeSH
• lidé MeSH
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Research Support, N.I.H., Extramural MeSH
• Názvy látek
• anthokyaniny MeSH
• cyanidin-3-O-beta-glucopyranoside MeSH Prohlížeč
• cytochrom P-450 CYP1A1 MeSH
• glukosidy MeSH
• inhibitory enzymů MeSH
• pelargonidin MeSH Prohlížeč
• receptory aromatických uhlovodíků MeSH

The anthocyanin composition of blue (Triticum aestivum L., cv. Skorpion) and purple wheat (Triticum aethiopicum JAKUBZ cv. Abyssinskaja arrasajta cv. Abyssinskaja arrasajta), cultivated in the Czech Republic, and of the prepared whole blue and purple wheat bread was determined. In blue and purple wheat, 19 and 26 anthocyanins, respectively, were tentatively identified by liquid chromatography and mass spectrometry. The total content of anthocyanins determined in blue and purple wheat was 9.26 and 13.23 mgkg(-1), respectively. The breads were baked at 240 and 180 °C. Some significant differences in anthocyanins content were observed between breads prepared at different baking temperatures. The content of cyanidin-3-glucoside, delphinidin-3-glucoside and pelargonidin-3-glucoside was determinated in starting material, whole meal flours and baked breads. These kinds of wheat are suitable for baking bread, since intake of anthocyanins may play an important role in the prevention of human diseases.

• Klíčová slova
• Bakery products, LC-MS, cereals, polyphenols, spectrophotometry,
• MeSH
• anthokyaniny analýza   chemie   MeSH
• chléb analýza   MeSH
• chromatografie kapalinová MeSH
• druhová specificita MeSH
• glukosidy analýza   MeSH
• hmotnostní spektrometrie s elektrosprejovou ionizací MeSH
• jedlá semena chemie   MeSH
• lidé MeSH
• mouka analýza   MeSH
• pšenice chemie   MeSH
• vaření * MeSH
• vysoká teplota * MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Geografické názvy
• Česká republika MeSH
• Názvy látek
• anthokyaniny MeSH
• glukosidy MeSH