Enhancement of the mutagenicity of polyphenols by chlorination and nitrosation in Salmonella typhimurium.
The hydrolytic products of lignins, humic acids and industrial waste including hydroquinone, catechol, resorcinol, pyrogallol and 1,2,4-benzenetriol are widely distributed in water sources. These polyphenols can interact with chlorine or nitrite to yield new derivatives. Generally, these new products possess more mutagenic potential than their original compounds. Furthermore, the mutagenicity of these polyphenols and their derivatives can be dramatically reduced by rodent liver microsomal enzymes (S9). The mutagenicity of polyphenols is in this order: hydroquinone greater than 1,2,4-benzenetriol greater than pyrogallol, while catechol, resorcinol and phloroglucinol are non-mutagenic. The ultimate product of chlorination or nitrosation of hydroquinone has been identified to be p-benzoquinone. The formation of active oxygen species including superoxide anion and hydrogen peroxide by polyphenols has been demonstrated and this may contribute partly to the molecular mechanisms of polyphenol mutagenicity.
Lin
J K
JK
Institute of Biochemistry, College of Medicine, National Taiwan University, Taipei.
Lee
S F
SF
D002396:Catechols / Q000494:pharmacology; D002713:Chlorine / Q000494:pharmacology*; D006861:Hydrogen Peroxide; D006873:Hydroquinones / Q000494:pharmacology*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000494:pharmacology*; D009573:Nitrites / Q000494:pharmacology*; D010636:Phenols / Q000494:pharmacology*; D010696:Phloroglucinol / Q000494:pharmacology; D012118:Resorcinols / Q000494:pharmacology; D012486:Salmonella typhimurium / Q000187:drug effects*; D013329:Structure-Activity Relationship
D002396:Catechols; D006873:Hydroquinones; D009153:Mutagens; D009573:Nitrites; D010636:Phenols; D012118:Resorcinols; C013038:hydroxyhydroquinone; D002713:Chlorine; D006861:Hydrogen Peroxide; D010696:Phloroglucinol; C034221:catechol; C031927:hydroquinone; C031389:resorcinol