Effects of 0, 1, 5, 25 and 125 μmol/g gallic acid (GA) without or with ultrasound treatment (20 kHz, 400 w, 5 min) (NU or U groups) on properties of Japanese seerfish myofibrillar protein (MP) were studied. After sonication, tryptophan fluorescence decreased while surface hydrophobicity, free amine and SH content (not U125) and solubility increased. After heating, NU125 showed the heaviest polymers among NU groups, but U5 exhibited the strongest while U125 showed the weakest polymers in U groups. Storage modulus (G') of NU groups showed a dose-dependent style, but for U groups, U5 had the highest G' while U125 had the lowest G'. Mass analysis confirmed the formation of Cys-GA-Cys and Lys-GA-Lys polymers in U125. Thus, ultrasound promoted structural unfolding and reactive groups exposure, producing GA quinone by triggering OH·. These together led to the G' improvement by low dose GA but deterioration by high does GA.
- Klíčová slova
- 2,4,6-Trinitrobenzenesulfonic acid (PubChem CID: 11045), 5,5′-Dithiobis-(2-nitrobenzoic acid) (PubChem CID: 6254), Amino-quinone adduct, Bromophenol blue (PubChem CID: 8272), Gallic acid, Gallic acid (PubChem CID: 370), Hydroxyl radical, Maleic acid (PubChem CID: 444266), Myofibrillar protein, N-Ethylmaleimide (PubChem CID: 4362), Rheological properties, Sodium dodecyl sulfate (PubChem CID: 3423265), Thiol-quinone adduct, Ultrasound, l-Leucine (PubChem CID: 6106), β-Mercaptoethanol (PubChem CID: 1567),
- MeSH
- hydrofobní a hydrofilní interakce MeSH
- kyselina gallová chemie MeSH
- rybí proteiny chemie MeSH
- ultrazvuk MeSH
- velikost částic MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- kyselina gallová MeSH
- rybí proteiny MeSH
Galloyl esters of quercetin and taxifolin have been recently prepared semisynthetically as part of work towards modifying the solubility and modulating the biological activity of these natural flavonoids. In this paper we focused on the liquid chromatography-mass spectrometry (LC-MS) profiling of metabolites of 3-O-galloylquercetin and 7-O-galloyltaxifolin using human hepatocytes as the in vitro cell model. A subtoxic concentration (50μM) was used for both compounds and the formation of metabolites was monitored for 2h in hepatocytes and cultivation medium separately. Using negative electrospray ionization-quadrupole time-of-flight mass spectrometry (ESI-QqTOF MS), we identified different biotransformation patterns for the studied compounds. 3-O-Galloylquercetin is metabolized directly to glucuronides and methyl derivatives. In contrast, 7-O-galloyltaxifolin is oxidized to 7-O-galloylquercetin or cleaved to taxifolin, and consequently the products formed are sulfated or glucuronidated. The oxidative biotransformation of 3-O-galloylquercetin and 7-O-galloyltaxifolin is also accompanied by ester bond cleavage presumably by cellular enzymes (esterases) in a nonspecific manner. Our results provide fundamental insights into the biotransformation of monogalloyl esters of flavonoids and can be applied in investigations of the pharmaceutical potential of other galloylated polyphenolic substances.
- Klíčová slova
- 3-O-galloylquercetin, 3-O-galloylquercetin glucuronide, 3-O-galloylquercetin methyl derivative, 3GQ, 3GQG, 3GQM, 7-O-galloylquercetin, 7-O-galloyltaxifolin, 7GQ, 7GT, Cytotoxicity, ESI-QqTOF MS, GA, HPLC, LC–MS, Mass spectrometry, Metabolic transformation, PHE, Quercetin-3-O-gallate, SIM, TG, TS, Taxifolin-7-O-gallate, electrospray ionization-quadrupole time-of-flight mass spectrometry, gallic acid (gallate), high-performance liquid chromatography, liquid chromatography–mass spectrometry, phenyl, selected-ion monitoring, taxifolin glucuronide, taxifolin sulfate,
- MeSH
- biotransformace MeSH
- buňky NIH 3T3 MeSH
- chromatografie kapalinová metody MeSH
- estery MeSH
- hepatocyty účinky léků metabolismus MeSH
- hmotnostní spektrometrie metody MeSH
- kultivované buňky MeSH
- kyselina gallová chemie farmakokinetika toxicita MeSH
- lidé středního věku MeSH
- lidé MeSH
- mladiství MeSH
- myši inbrední BALB C MeSH
- myši MeSH
- quercetin analogy a deriváty chemie farmakokinetika toxicita MeSH
- tandemová hmotnostní spektrometrie metody MeSH
- zvířata MeSH
- Check Tag
- lidé středního věku MeSH
- lidé MeSH
- mladiství MeSH
- mužské pohlaví MeSH
- myši MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- estery MeSH
- kyselina gallová MeSH
- quercetin MeSH
- quercitrin MeSH Prohlížeč
- taxifolin MeSH Prohlížeč
Complete separation of aglycones and glucosides of selected isoflavones (genistin, genistein, daidzin, daidzein, glycitin, glycitein, ononin, sissotrin, formononetin, and biochanin A) was possible in 1.5 min using an ultrahigh-pressure liquid chromatography (U-HPLC) on a different particular chemically modified stationary phases with a particle size under 2 microm. In addition, selected separation conditions for simultaneous determination of isoflavones together with a group of phenolic acids (gallic, protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, and sinapic acid) allowed separation of all 19 compounds in 1.9 min. Separations were conducted on a non-polar reversed phase (C(18)) and also on more polar phases with cyanopropyl or phenyl groups using a gradient elution with a mobile phase consisting of 0.3% aqueous acetic acid and methanol. Chromatographic peaks were characterised using parameters such as resolution, symmetry, selectivity, etc. Individual substances were identified and quantified using UV-vis diode array detector at wavelength 270 nm. Limits of detection (3S/N) were in the range 200-400 pg ml(-1). Proposed U-HPLC technique was used for separation of isoflavones and phenolic acids in samples of plant materials (Trifolium pratense, Glycine max, Pisum sativum and Ononis spinosa) after acid hydrolysis of the samples and modified Soxhlet extraction.
- MeSH
- genistein chemie izolace a purifikace MeSH
- Glycine max chemie MeSH
- hrách setý chemie MeSH
- hydroxybenzoáty chemie izolace a purifikace MeSH
- isoflavony chemie izolace a purifikace MeSH
- kyselina gallová analogy a deriváty chemie izolace a purifikace MeSH
- kyselina vanilová chemie izolace a purifikace MeSH
- kyseliny kávové chemie izolace a purifikace MeSH
- kyseliny kumarové chemie izolace a purifikace MeSH
- molekulární struktura MeSH
- propionáty MeSH
- rostlinné extrakty chemie izolace a purifikace MeSH
- Trifolium chemie MeSH
- vysokoúčinná kapalinová chromatografie metody MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- biochanin A MeSH Prohlížeč
- caffeic acid MeSH Prohlížeč
- daidzein MeSH Prohlížeč
- daidzin MeSH Prohlížeč
- ferulic acid MeSH Prohlížeč
- formononetin MeSH Prohlížeč
- genistein MeSH
- genistin MeSH Prohlížeč
- glycitein MeSH Prohlížeč
- glycitin MeSH Prohlížeč
- hydroxybenzoáty MeSH
- isoflavony MeSH
- kyselina gallová MeSH
- kyselina vanilová MeSH
- kyseliny kávové MeSH
- kyseliny kumarové MeSH
- p-coumaric acid MeSH Prohlížeč
- phenolic acid MeSH Prohlížeč
- propionáty MeSH
- protocatechuic acid MeSH Prohlížeč
- rostlinné extrakty MeSH
- sinapinic acid MeSH Prohlížeč
- syringic acid MeSH Prohlížeč