Condensation of anthocyanins and their aglycons with small organic molecules yields more stable natural dyes, e.g. pyranoanthocyanins arising spontaneously in various food products. Reaction of pelargonidin with acetone produces two isomeric anthocyanidin dyes - 5-methylpyranopelargonidin and 4-methylfuropelargonidin. A robust semipreparative liquid chromatographic method was developed to isolate both derivatives from a simple aged solution of pelargonidin in methanol: acetone: 37% aqueous hydrochloric acid (1:1:0.008, v/v/v). Detailed interpretation of mass and nuclear magnetic resonance spectra allowed to assign structures of both dyes in isolated fractions. A fast UHPLC-MS method was optimized for the control of their production in the reaction mixture. Use of reversed stationary phase and acidic mobile phases in gradient mode allowed separation of both isomers in less than one minute. Fragmentation of both dyes after collision activated dissociation in collision cell was studied comprehensively and the observed processes were compared with data from quantum calculations (computational chemistry utilizing DFT methods). When comparing both isomers, retro-Diels-Alder fragmentation appears preferred in furo-derivative, while small losses (i.e. methane and water molecules) were more pronounced in pyrano-derivative. Both studied isomeric dyes were found in laboratory prepared strawberry fruit wine and their content was compared with major present anthocyanins and their derivatives.
- MeSH
- anthokyaniny analýza chemická syntéza izolace a purifikace MeSH
- barvicí látky analýza chemická syntéza izolace a purifikace MeSH
- chemické techniky analytické metody MeSH
- jahodník * chemie MeSH
- ovoce chemie MeSH
- víno analýza MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články 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.
- 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
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.
Borůvka černá (dříve označována jako brusnice borůvka) je známá především díky chutným plodům, které mají schopnost barvit do modra, za což jsou zodpovědné látky zvané antokyaniny. V lidovém léčitelství se užívá list, nať a plod k léčbě diabetu, kardiovaskulárních chorob, demence a rakoviny. Antidiabeticky působí především antokyaniny a polyfenoly. Tyto obsahové látky v klinických studiích vykazují přímé antidiabetické účinky mechanismem zvýšení sekrece insulinu (antokyanin pelargonidin), snížení insulinové rezistence (antokyanin cyanidin-3-glukosid), snížení resorpce glukosy GIT (polyfenoly) a zvýšení regenerace B-buněk. Antokyaniny dále působí ke zlepšení lipidového spektra, antioxidačně, protizánětlivě a kardioprotektivně. Antidiabetické účinky antokyaninu cyanidin-3-galaktosidu bylo srovnáváno s akarbosou (působí synergicky), hypocholesterolemické účinky cyanidin-3-O-glukosidu byly srovnávány s atorvastatinem (působí synergicky) a hypolipidemické účinky extraktu z listů z borůvek byly srovnávány s ciprofibrátem (extrakt z listů je méně účinný). Nicméně, v preklinických a klinických studiích byly zahrnuty i jiné druhy rodu Vaccinium a další rostliny obsahující obdobné látky s obdobnými účinky jako Vaccinium myrtillus. Pro přesvědčivé stanovení účinnosti abezpečnosti léčby fytopreparáty z borůvky však bude nutné provést další studie kobjasnění, které typy antokyaninů jsou nejvhodnější pro léčbu, stanovit jejich optimální dávky aporovnat účinnost extraktů čistých antokyaninů ve vztahu ke konzumaci na antokyaniny bohatých potravin. Klíčová slova: borůvka černá • Vaccinium myrtillus • diabetes mellitus • fytoterapie • antokyaniny
The billberry is well-known for its tasty blue-dyeing fruits. Historically the leaves and fruits were used to treat diabetes, cardiovascular diseases, dementia and cancer. Antidiabetic properties of the plant are attributed mostly to the content of anthocyanins and polyphenols. These compounds have proven their antidiabetic potential in various studies. Their mechanism of action is an increase in insulin secretion (anthocyanin pelargonidin), reduction of insulin resistance (anthocyanin cyanidin-3-glucoside), glucose resorption from the GIT (polyphenols) and enhancement of beta-cells regeneration. Besides these effects, anthocyanins contribute to the improvement of the lipid spectrum and have antioxidant, anti-inflammatory and cardioprotective activities. Antidiabetic effects of anthocyanin cyanidin-3-galactoside were compared to acarbose (synergistic effect), hypocholesterolemic activity of cyanidin-3-O-glucoside to atorvastatin (synergistic effect) and hypolipidemic properties of blueberry leaf extract to ciprofibrate (extract has a lower effect). However, in many preclinical and clinical studies different species of the Vaccinium genus and other plants with asimilar effect as the billberry were also assessed. Therefore, in order to convincingly assess the efficacy and safety of blueberry herbal medicines more studies are necessary. Such studies should shed light into the variety of anthocyanins, their particular effects and optimal doses and compare their effects with intake of foods generally rich in anthocyanins. Key words: billberry • Vaccinium myrtillus • diabetes mellitus • phytotherapy • antocyanines
- MeSH
- anthokyaniny izolace a purifikace terapeutické užití MeSH
- diabetes mellitus 2. typu * farmakoterapie MeSH
- fytoterapie využití MeSH
- jídelníček MeSH
- krysa rodu rattus MeSH
- lidé MeSH
- modely u zvířat MeSH
- polyfenoly MeSH
- preklinické hodnocení léčiv MeSH
- rostlinné extrakty terapeutické užití MeSH
- techniky in vitro MeSH
- Vaccinium myrtillus * MeSH
- výsledek terapie MeSH
- Check Tag
- krysa rodu rattus MeSH
- lidé MeSH
- Publikační typ
- práce podpořená grantem MeSH
The aim of this work was to study the effect of the daily ingestion of a purified anthocyanin extract from red grape skin on rat serum antioxidant capacity (ORAC) and its safety for the intestinal epithelium. The study was carried out in rats orally administered with the extract for 10 days in either normal physiological conditions or exposed to a pro-oxidant chemical (CCl(4)). The oral administration of the extract significantly (P<0.05) enhanced the ORAC value of the deproteinised serum of about 50 % after 10 days of ingestion. Anthocyanin administration was also able to reverse completely the decrease in the serum ORAC activity induced by the CCl(4) treatment. Experiments with Ussing chamber mounted intestine allowed to exclude any toxicity of the extract for the intestinal epithelium. In conclusion, our results demonstrate that the purified anthocyanin extract from red grape skin enhances the total antioxidant capacity of the serum in either normal physiological condition or during oxidative stress induction, revealing a protective role against the decrease in the serum antioxidant capacity induced by a pro-oxidant compound.
- MeSH
- anthokyaniny aplikace a dávkování izolace a purifikace krev MeSH
- antioxidancia metabolismus MeSH
- biologické markery krev MeSH
- jejunum metabolismus účinky léků MeSH
- krysa rodu rattus MeSH
- potkani Wistar MeSH
- rostlinné extrakty aplikace a dávkování izolace a purifikace MeSH
- sérum fyziologie MeSH
- Vitis MeSH
- zvířata MeSH
- Check Tag
- krysa rodu rattus MeSH
- mužské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- práce podpořená grantem MeSH
- srovnávací studie MeSH
Anthocyanins from the fruit Lonicera caerulea L. var. kamtschatica (blueberry honeysuckle, Caprifoliaceae) were studied via (semi)preparative chromatographic fractionation followed by MS and μLC/MS analysis. The extraction procedure was optimized with respect to analytical purposes as well as its potential use for the preparation of nutraceuticals. The highest yield of anthocyanins was obtained using acidified methanol as the extraction medium. A comparable total anthocyanin content was obtained using a mixture of methanol and acetone. However, when Lonicera anthocyanins were in contact with acetone, a condensation reaction occurred to a large extent and related 5-methylpyranoanthocyanins were found. The effect of other extraction media, including ethanol as a "green" solvent, is also discussed. The potential of two fractionation procedures for extract purification differing in their chromatographic selectivity and scale was studied (i.e. using a Sephadex LH-20 gel column and a reversed phase). Fractions obtained by both procedures were used for a detailed analysis. MS and μLC/MS(2) methods were used for monitoring anthocyanin and 5-methylpyranoderivatives content as well as identifying less common and more complex dyes (dimer of cyanidin-3-hexoside, cyanidin-ethyl-catechin-hexosides, etc.). These more complex dyes are most likely formed during fruit treatment.
- MeSH
- anthokyaniny analýza izolace a purifikace MeSH
- chemická frakcionace přístrojové vybavení metody MeSH
- Lonicera chemie MeSH
- rostlinné extrakty analýza izolace a purifikace MeSH
- tandemová hmotnostní spektrometrie metody MeSH
- vysokoúčinná kapalinová chromatografie přístrojové vybavení metody MeSH
- Publikační typ
- časopisecké články MeSH
- hodnotící studie MeSH
- práce podpořená grantem MeSH
