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Reactive oxygen species (ROS) play a major role in carcinogenesis: pro-oxidant agents like tobacco smoke, asbestos or N-nitrosamines, are known as mutagenic and carcinogenic, and cancer cells show increased levels of ROS and redox deregulation. However, pro-oxidant molecules can also act as selective cytotoxic agents against cancer cells by achieving toxic levels of ROS. Although polyphenols are well-known as potent antioxidants, a pro-oxidant effect has been associated with their pro-apoptotic effect in various types of tumor cells. The aim of the present review is to present the main evidences of the pro-oxidant-related cytotoxic activity of naturally occurring polyphenols and their underlying mechanisms.