Effect of flavonoids on 2'-deoxyguanosine and DNA oxidation caused by singlet molecular oxygen.
Antioxidant potential is generally investigated by assaying the ability of a compound to protect biological systems from free radicals. However, non-radical reactive oxygen species can also be harmful. Singlet molecular oxygen ((1)O(2)) is generated by energy transfer to molecular oxygen. The resulting (1)O(2) is able to oxidize the nucleoside 2'-deoxyguanosine (dGuo), which leads to the formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodGuo) and spiroiminodihydantoin 2'-deoxyribonucleoside diastereomers (dSp) in an aqueous solution. The main objective of the present study was to verify whether the presence of flavonoids (flavone, apigenin, quercetin, morin and catechin) at different concentrations could protect dGuo from (1)O(2) damage. Of the tested flavonoids, flavone possessed antioxidant activity, as determined by a decrease in the formation of both products. Apigenin, morin, quercetin and catechin all increased the formation of 8-oxodGuo at a concentration of 100 microM. The quantification of plasmid strand breaks after treatment with formamidopyrimidine-DNA glycosylase showed that flavone protected and quercetin and catechin enhanced DNA oxidation. Our results show that compounds, such as flavonoids, may affect the product distribution of (1)O(2)-mediated oxidation of dGuo, and, in particular, high concentrations of flavonoids with hydroxyl groups in their structure lead to an increase in the formation of the mutagenic lesion 8-oxodGuo.
Carneiro
Carlos D
CD
Departamento de Bioquímica e Biologia Molecular, Setor de Ciências Biológicas, Universidade Federal do Paraná, Brazil.
Amorim
Juliana C
JC
Cadena
Silvia M S C
SM
Noleto
Guilhermina R
GR
Di Mascio
Paolo
P
Rocha
Maria E M
ME
Martinez
Glaucia R
GR
D000975:Antioxidants / Q000494:pharmacology*; D047310:Apigenin / Q000737:chemistry; D002392:Catechin / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000187:drug effects*; D003849:Deoxyguanosine / Q000378:metabolism*; D004591:Electrophoresis, Polyacrylamide Gel; D047309:Flavones / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D009281:Naphthalenes / Q000737:chemistry; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry; D011794:Quercetin / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D000975:Antioxidants; D047309:Flavones; D005419:Flavonoids; D009281:Naphthalenes; D010545:Peroxides; D017382:Reactive Oxygen Species; C031721:naphthalene; D047310:Apigenin; C008548:morin; D002392:Catechin; D004247:DNA; D011794:Quercetin; D003849:Deoxyguanosine