Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine).
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.
Liu
X
X
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.
Zang
L
L
Van der Schyf
C J
CJ
Igarashi
K
K
Castagnoli
K
K
Castagnoli
N
N
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*
D005609:Free Radicals; D007306:Insecticides; D011725:Pyridines; D011758:Pyrroles; C008615:alpha-nicotyrine