Prooxidant activity of flavonoids: copper-dependent strand breaks and the formation of 8-hydroxy-2'-deoxyguanosine in DNA.
The naturally occurring flavonoids caused strand scission of DNA in the presence of copper ion. Flavonoids such as myricetin, baicalein, and quercetin as well as ascorbic acid cleaved plasmid pBR322 DNA and calf thymus DNA potently. Addition of catalase protected DNA from the strand breaks caused by flavonoids. Treatment of calf thymus DNA with these flavonoids or ascorbate plus copper produced 8-hydroxy-2'-deoxyguanosine. Cuprous ion reduced by flavonoids and ascorbic acid may play a key role in the oxidative cleavage of DNA and the formation of base adduct. Mutagenic and carcinogenic action of flavonoids may be explained by the prooxidant effects of the compounds.
Yoshino
M
M
Department of Biochemistry, Central Research Laboratories, Aichi Medical University, Nagakute, Aichi, 480-1195, Japan.
Haneda
M
M
Naruse
M
M
Murakami
K
K
D000080242:8-Hydroxy-2'-Deoxyguanosine; D000818:Animals; D000975:Antioxidants / Q000737:chemistry; D001205:Ascorbic Acid / Q000737:chemistry; D002417:Cattle; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D004249:DNA Damage; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry*; D009153:Mutagens / Q000737:chemistry*; D010084:Oxidation-Reduction; D010957:Plasmids
D000975:Antioxidants; D005419:Flavonoids; D009153:Mutagens; D003300:Copper; D000080242:8-Hydroxy-2'-Deoxyguanosine; D004247:DNA; D003849:Deoxyguanosine; D001205:Ascorbic Acid