BIOSYNTHESIS OF PINIDINE

The administration of sodium acetate-1-14C to Pinus jeffreyi plants afforded radioactive pinidine (2-methyl-6-(2-trans-propenyl)piperidine). A systematic degradation of the alkaloid indicated that almost all the radioactivity was located on carbon atoms 2, 4, 6, and 9, and was equally distributed between these positions. This result favors the hypothesis that this piperidine alkaloid is derived from a ten-carbon chain formed by the linear combination of five acetate units. Pinidine isolated from plants which had been fed dl-lysine-2-14C was also radioactive; however, a partial degradation of this labeled pinidine indicated that the activity was not confined to the piperidine ring. The pattern of labeling was consistent with catabolism of the lysine-2-14C to acetic acid-1-14C which was then incorporated as previously postulated. © 1969, American Chemical Society. All rights reserved.