• Je něco špatně v tomto záznamu ?

Redox properties of individual quercetin moieties

E. Heřmánková, M. Zatloukalová, M. Biler, R. Sokolová, M. Bancířová, AG. Tzakos, V. Křen, M. Kuzma, P. Trouillas, J. Vacek,

. 2019 ; 143 (-) : 240-251. [pub] 20190802

Jazyk angličtina Země Spojené státy americké

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/bmc20025532

Quercetin is one of the most prominent and widely studied flavonoids. Its oxidation has been previously investigated only indirectly by comparative analyses of structurally analogous compounds, e.g. dihydroquercetin (taxifolin). To provide direct evidence about the mechanism of quercetin oxidation, we employed selective alkylation procedures for the step-by-step blocking of individual redox active sites, i.e. the catechol, resorcinol and enol C-3 hydroxyls, as represented by newly prepared quercetin derivatives 1-3. Based on the structure-activity relationship (SAR), electrochemical, and computational (density functional theory) studies, we can clearly confirm that quercetin is oxidized in the following steps: the catechol moiety is oxidized first, forming the benzofuranone derivative via intramolecular rearrangement mechanism; therefore the quercetin C-3 hydroxy group cannot be involved in further oxidation reactions or other biochemical processes. The benzofuranone is oxidized subsequently, followed by oxidation of the resorcinol motif to complete the electrochemical cascade of reactions. Derivatization of individual quercetin hydroxyls has a significant effect on its redox behavior, and, importantly, on its antiradical and stability properties, as shown in DPPH/ABTS radical scavenging assays and UV-Vis spectrophotometry, respectively. The SAR data reported here are instrumental for future studies on the oxidation of biologically or technologically important flavonoids and other polyphenols or polyhydroxy substituted aromatics. This is the first complete and direct study mapping redox properties of individual moieties in quercetin structure.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc20025532
003      
CZ-PrNML
005      
20201222155242.0
007      
ta
008      
201125s2019 xxu f 000 0|eng||
009      
AR
024    7_
$a 10.1016/j.freeradbiomed.2019.08.001 $2 doi
035    __
$a (PubMed)31381971
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a xxu
100    1_
$a Heřmánková, Eva $u Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20, Prague, Czech Republic.
245    10
$a Redox properties of individual quercetin moieties / $c E. Heřmánková, M. Zatloukalová, M. Biler, R. Sokolová, M. Bancířová, AG. Tzakos, V. Křen, M. Kuzma, P. Trouillas, J. Vacek,
520    9_
$a Quercetin is one of the most prominent and widely studied flavonoids. Its oxidation has been previously investigated only indirectly by comparative analyses of structurally analogous compounds, e.g. dihydroquercetin (taxifolin). To provide direct evidence about the mechanism of quercetin oxidation, we employed selective alkylation procedures for the step-by-step blocking of individual redox active sites, i.e. the catechol, resorcinol and enol C-3 hydroxyls, as represented by newly prepared quercetin derivatives 1-3. Based on the structure-activity relationship (SAR), electrochemical, and computational (density functional theory) studies, we can clearly confirm that quercetin is oxidized in the following steps: the catechol moiety is oxidized first, forming the benzofuranone derivative via intramolecular rearrangement mechanism; therefore the quercetin C-3 hydroxy group cannot be involved in further oxidation reactions or other biochemical processes. The benzofuranone is oxidized subsequently, followed by oxidation of the resorcinol motif to complete the electrochemical cascade of reactions. Derivatization of individual quercetin hydroxyls has a significant effect on its redox behavior, and, importantly, on its antiradical and stability properties, as shown in DPPH/ABTS radical scavenging assays and UV-Vis spectrophotometry, respectively. The SAR data reported here are instrumental for future studies on the oxidation of biologically or technologically important flavonoids and other polyphenols or polyhydroxy substituted aromatics. This is the first complete and direct study mapping redox properties of individual moieties in quercetin structure.
650    _2
$a antioxidancia $x chemie $7 D000975
650    _2
$a scavengery volných radikálů $x chemie $7 D016166
650    _2
$a oxidace-redukce $7 D010084
650    _2
$a quercetin $x chemie $7 D011794
650    _2
$a vztahy mezi strukturou a aktivitou $7 D013329
655    _2
$a časopisecké články $7 D016428
655    _2
$a práce podpořená grantem $7 D013485
700    1_
$a Zatloukalová, Martina $u Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 775 15, Olomouc, Czech Republic.
700    1_
$a Biler, Michal $u INSERM U1248, Univ. Limoges, 2 rue du Docteur Marcland, 87025, Limoges, France.
700    1_
$a Sokolová, Romana $u J. Heyrovský Institute of Physical Chemistry of the Czech Academy of Sciences, Dolejškova 3, 182 23, Prague 8, Czech Republic.
700    1_
$a Bancířová, Martina $u Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 775 15, Olomouc, Czech Republic.
700    1_
$a Tzakos, Andreas G $u Department of Chemistry, University of Ioannina, Ioannina, 45110, Greece.
700    1_
$a Křen, Vladimír $u Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20, Prague, Czech Republic. Electronic address: kren@biomed.cas.cz.
700    1_
$a Kuzma, Marek $u Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20, Prague, Czech Republic.
700    1_
$a Trouillas, Patrick $u INSERM U1248, Univ. Limoges, 2 rue du Docteur Marcland, 87025, Limoges, France; RCPTM, Palacký University, 17. listopadu 1192/12, Olomouc, Czech Republic.
700    1_
$a Vacek, Jan $u Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 775 15, Olomouc, Czech Republic. Electronic address: jan.vacek@upol.cz.
773    0_
$w MED00001857 $t Free radical biology & medicine $x 1873-4596 $g Roč. 143, č. - (2019), s. 240-251
856    41
$u https://pubmed.ncbi.nlm.nih.gov/31381971 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y a $z 0
990    __
$a 20201125 $b ABA008
991    __
$a 20201222155238 $b ABA008
999    __
$a ok $b bmc $g 1599677 $s 1116218
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2019 $b 143 $c - $d 240-251 $e 20190802 $i 1873-4596 $m Free radical biology & medicine $n Free Radic Biol Med $x MED00001857
LZP    __
$a Pubmed-20201125

Najít záznam

Citační ukazatele

Možnosti archivace