Identification of adducts formed by reaction of purine bases with a mutagenic anthraquinone, lucidin: mechanism of mutagenicity by anthraquinones occurring in rubiaceae plants.
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 approximately 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.
Kawasaki
Y
Y
National Institute of Health Sciences, Tokyo, Japan.
Goda
Y
Y
Noguchi
H
H
Yamada
T
T
D000880:Anthraquinones / Q000378:metabolism* / Q000633:toxicity*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000378:metabolism* / Q000633:toxicity*; D010936:Plant Extracts / Q000378:metabolism* / Q000633:toxicity*; D010946:Plants, Medicinal / Q000737:chemistry; D011687:Purines / Q000378:metabolism*; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D009153:Mutagens; D010936:Plant Extracts; D011687:Purines; C039315:lucidin