Abstract
Ptaquiloside (1) is a potent carcinogen isolated from bracken fern. Under weakly alkaline conditions, the carcinogen is converted into dienone 2 which is thought to be the ultimate agent responsible for bracken fern carcinogenicity. This study details the selective alkylation and strand scission of DNA with dienone 2. Dienone 2 forms covalent adducts through N-3 of adenine or N-7 of guanine with opening of the cyclopropyl ring. Under physiological conditions, spontaneous cleavage of the N-glycosidic linkage occurs primarily at the modified adenines to produce abasic sites. The abasic sites are so unstable that subsequent backbone breakage occurs via a β-elimination reaction
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