Phytochemical Studies on the Tobacco Alkaloids

Part VIII. Biosynthesis of the Pyrrolidine Ring of Nornicotine in the Excised Root Culture

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Duplicate feeding experiments of dl-ornithine-2-¹⁴C to the excised tobacco root culture were made, and the radioactive nornicotine was isolated. Approximately two thirds of the radioactivity was located in the 2-position of the pyrrolidine of the nornicotine in these experiments. This fact indicates that there are two modes in nornicotine biosynthesis: exclusive incorporation to the C-2 and equal incorporation to C-2 and C-5 from C-2 of ornithine.
On the basis of this finding, biosynthetic route was discussed.