IDENTIFICATION OF ADDUCTS FORMED BY REACTION OF PURINE BASES WITH A MUTAGENIC ACTHRAQUINONE, LUCIDIN : MECHANISM OF MUTAGENICITY BY ANTHRAQUINONES OCCURING IN RUBIACEAE PLANTS

Abstract

A mutagenic anthraquinone, lucidin (1), occurring in Rubiaceae plants, reacted with nucleic bases under physiological conditions to form adducts. The order of the reactivity is as follows : adenine>guanine ⪼pyrimidine bases _∼0. By spectroscopic analyses, the isolated purine base adducts were identified as condensed reactants at the benzylic position of 1 with a nitrogen atom of a purine base. The results indicate a strong possibility of the formation of an exomethylenic compound as an electrophile intermediate.