Cooh

anabasine

bipyridyl

N-isopentyl-2-phenylethylamine

Figure 9.4 The biosynthesis of nicotine from ornithine and nicotinic acid. Anabasine, anabaseine and bipyridyl, all ant alkaloids, are made by plants using lysine in place of ornithine. Cotinine is a metabolite of nicotine, N-isopentyl-2-phenylethylamine is an important constituent of the trail pheromone of the ant Aphaenogaster rudis bipyridyl

N-isopentyl-2-phenylethylamine

Figure 9.4 The biosynthesis of nicotine from ornithine and nicotinic acid. Anabasine, anabaseine and bipyridyl, all ant alkaloids, are made by plants using lysine in place of ornithine. Cotinine is a metabolite of nicotine, N-isopentyl-2-phenylethylamine is an important constituent of the trail pheromone of the ant Aphaenogaster rudis

The alkylpiperidines and tetrahydropyridines form a powerful venom in Solenopsis ants (Figure 9.5). The sting of these ants is so painful, they are known as fire ants. Both cis and trans arrangements of the methyl and alkyl groups are found; the ds-linked are always (R, S) and the trans are (R,R). Because S. geminata makes essentially only cis- and trans-solenopsin A, it was chosen for the biosynthesis experiments. Other species make more complicated mixtures. Feeding experiments with 3,000 to 4,000 Solenopsis geminata, using sodium [l-14C]-acetate and

2-methyl-6-alkyl-piperidines n = 6 to 14

2Jn n = 3, 5 or 7 2-methyl-6-alkenylpiperidines chp

N^JTo

2-methyl-6-alkyl-tetrahydropyridines

0 0

Post a comment