Identification of adducts formed by reaction of purine bases with a mutagenic anthraquinone, 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. © 1994, The Pharmaceutical Society of Japan. All rights reserved.