title: Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine).
abstract: Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (beta-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the chemically stable 5-hydroxy-5-(3-pyridinyl)-3-pyrrolin-2-one. This paper summarizes efforts to document more completely the pathway leading to this hydroxypyrrolinone. Chemical and spectroscopic evidence implicates the 2-hydroxy-1-methyl-5-(3-pyridinyl)pyrrole (2-hydroxy-beta-nicotyrine) as the key intermediate in this reaction pathway. Of potential toxicological interest is the detection of radical species derived from the autoxidation of this compound.
authors.affiliation: Peters Center for the Study of Parkinson's Disease, Department of Chemistry, VA-MD Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA.
authors.forename: X
authors.initials: X
authors.lastname: Liu
authors.forename: L
authors.initials: L
authors.lastname: Zang
authors.forename: C J
authors.initials: CJ
authors.lastname: Van der Schyf
authors.forename: K
authors.initials: K
authors.lastname: Igarashi
authors.forename: K
authors.initials: K
authors.lastname: Castagnoli
authors.forename: N
authors.initials: N
authors.lastname: Castagnoli
mesh_terms: D000818:Animals; D005609:Free Radicals; D007306:Insecticides / Q000378:metabolism*; D010084:Oxidation-Reduction; D010947:Plants, Toxic; D011725:Pyridines / Q000378:metabolism*; D011758:Pyrroles / Q000378:metabolism*; D011817:Rabbits; D014026:Nicotiana / Q000378:metabolism*
chemical_list: D005609:Free Radicals; D007306:Insecticides; D011725:Pyridines; D011758:Pyrroles; C008615:alpha-nicotyrine