Mechanism of cytotoxicity of catechols and a naphthalenediol in PC12-AC cells: the connection between extracellular autoxidation and molecular electronic structure

trans-Resveratrol induces apoptosis in human breast cancer cells MCF-7 by the activation of MAP kinases pathways

“…In addition, polyphenols have been proposed to induce oxidative stress indirectly by targeting mitochondrial electron transport chain, thereby generating a downstream flux of ROS [26,48]. In agreement with previous works, which identified a role for oxyradicals in cytotoxicity of polyphenols [6,46,19], we observed an early increase of ROS levels after treatment with high doses of trans-resveratrol in human breast cancer cells MCF-7.…”

“…Previous studies have indicated that some nutraceuticals exhibit potent anti-tumor properties and can modulate apoptosis, differentiation and cell cycle, probably by virtue of their anti-oxidant functions. However, in vitro experiments reported that most of them behave as potent pro-oxidants molecules [6,9,40]. For example, organosulfur molecules from garlic, such as the oil-soluble diallyl disulfide [12,13], diallyl trisulfide [22], or the water-soluble S-allylmercaptocysteine [63] have been demonstrated to induce growth arrest and apoptosis dose-dependently by increasing ROS production.…”

A Comparison Between Lignans from Creosote Bush and Flaxseed and Their Potential to Inhibit Cytochrome P450 Enzyme Activity

“…The autoxidation of NDGA to a reactive intermediate in rat hepatic microsomes (Billinsky et al, 2007) did not result in the inactivation of P450 enzyme activity. These findings are not unexpected as the literature suggests ortho-quinones do not usually undergo adduct formation with cellular macromolecules, instead their damage is usually mediated through an increase in oxidative stress (Chichirau et al, 2005;O'Brien 1991;Monks et al, 1992). Although ortho-quinones may isomerize to para-quinone methides in vivo, a quinone derivative known to form covalent adducts with cellular macromolecules (Powis 1987), this process is unlikely to occur as NDGA is substituted at the benzylic carbon, which severely hinders the isomerization process (Iverson et al, 1995).…”

Investigation of the electrochemical behavior of some catechols in the presence of 4,6-dimethylpyrimidine-2-thiol

“…3 Because electrochemical oxidation very often parallels the oxidation of catechols in the mammalian central nervous system and this process occurs in the human body 4 it was interesting to study the anodic oxidation of catechols in the presence of various nucleophiles. 5 The quinones formed are quite reactive and can be attacked by nucleophiles such as: methanol, 6 4-hydroxycoumarin, 7 4-hydroxy-6-methyl-2-pyrone, 8 6-methyl-1,2,4-triazine-3-thion-5-one 9 and so on.…”