Nicotine Synthesis Research Articles

Relation between the Behaviour of Nitrogen and the Nicotine Synthesis in Tobacco Plant

Abstract Nicotine of tobacco plant is synthesized in the root and accumulated mainly in the leaves. At the repening stage when the nicotine accumalation is predominant, the amount of nitrogen absorbed from root seemed to be little. It is believed, therefore, that the nitrogen used on nicotine synthesis would originate from the nitrogen which has been absorbed already bely fore repening. This has been reported previously by the authors (1). However if nitrogen absorption is increased during the ripening stage, this causes more nicotine synthesis (1,2).

Behavior of Nutrients Absorbed b Tobacco Plant (Part 3) : Relation between the Behavior of Nitrogen and the Nicotine Synthesis in Tobacco Plant

Behavior of Nutrients Absorbed b Tobacco Plant (Part 3) : Relation between the Behavior of Nitrogen and the Nicotine Synthesis in Tobacco Plant

Influences of Nitrogen nutrition on nicotine synthesis in tobacco plant

Abstract The synthesis of nicotine which is nitrogen containing compound in tobacco plant is accompanied with the nitrogen consumption. It is, therefore, natural that the level of nitrogen nutrition has a great influence on the nicotine synthesis. Generally, it has been recognized that the nicotine content was increased with increasing supply of nitrogen fertilizer (1).

A possible common biogenetic origin of the nicotine, tropane and hygrine bases.

THE isolation of both hyoscine and nicotine from a genotype of Duboisia myoporoides1 suggests the possibility of a close biosynthetic relation between these bases, and is consequently of interest in connexion with the classical schemes of alkaloid biogenesis2. However, a synthesis of nicotine or a related compound under so-called physiological conditions has not yet been effected, and it seems desirable to consider a possible alternative mechanism.

Nicotine Synthesis in Excised Tobacco Roots

Nicotine Synthesis in Excised Tobacco Roots

INFLUENCE OF CERTAIN AMINO ACIDS AND OF NICOTINIC ACID UPON THE NICOTINE CONTENT OF TOBACCO LEAVES

The tobacco alkaloid nicotine possesses a molecular structure by which it may be related empirically to the amino acid proline. Proline is a-pyrrolidinecarboxylic acid. Nicotine may be considered as an N-methylated proline containing a ?-pyridine ring attached to the alpha position in place of the carboxyl. These similarities have been pointed out by Tottingham (9) and have been employed by Trier (12) as a basis for extensive speculations on the probable origin of nicotine in the tobacco plant. According to Trier, nicotine may be formed in vivo from proline and nicotinic acid by a simultaneous oxidative decarboxylation of the two molecules. The methylation of the pyrrolidine nitrogen was accounted for by the action of methyl alcohol as a dismutation product of formaldehyde. Trier postulated the formation of the pyridine portion of the nicotine molecule from proline through the intervention of formic acid as the second dismutation product of formaldehyde. In short, the hypothesis of Trier assigned to proline the r?le of precursor of both the fiveand the six-member ed rings of the nicotine molecule. It should be noted, however, that Trier's theory was advanced at a time when nicotinic acid was practically unknown in the literature of plant chemistry. Klein and Linser (7) tested Trier's hypothesis by culturing the excised leafy shoots of tobacco plants in dilute aqueous solutions of proline. These investigators obtained large increases in the nicotine content of the leaves and stems of the plants to which proline had been supplied. The hydrochlorides of glutamic acid and of ornithine were found to possess similar effects. Gorter (5) critically reviewed the work of Klein and Linser and presented data of his own to show that both those plants provided with proline and those cultured in Knop's solution after a period of 4 or 5 days contained less nicotine than at the beginning of the experiment. The. increase in nicotine content of the leaves of the plants supplied with proline was only apparent and represented merely a less extensive decrease rather than an actual synthesis of nicotine. In the present study attention was given to the influences of proline, pyrrolidonecarboxylic acid, glutamic acid, ornithine, nicotinic acid, and other substances upon the nicotine content of tobacco leaves by the use of methods of culture and of expression of data

Nitrogen Nutrition and Nicotine Synthesis in Tobacco

1. The influence of ammonium, nitrate, and urea nitrogen upon nicotine synthesis in tobacco leaves has been investigated under conditions unfavorable for optimum carbohydrate formation. 2. Ammonium nitrogen compared with nitrate seemed definitely to have increased the relative nicotine content of tobacco leaves in the earlier stages of growth. This influence was soon lost, under the conditions of the experiments, and the ammonium-cultured plants, although lower in dry weight and showing definite indications of ammonium toxicity, subsequently possessed nicotine concentrations indistinguishable from those attained by the nitrate-cultured plants of the same age. 3. No essential difference was observed between the effects of "concentrated" and "dilute" ammonium nitrogen upon plant growth and dry weight. However, the nicotine content responded to the increased nitrogen supply of the concentrated ammonium solutions by assuming somewhat higher proportions in the leaves. 4. Growth of plants supplied only with urea nitrogen was inferior to the growth of plants cultured in ammonium solutions, either at concentrations of ammonium equivalent to or half that of the urea. The influence of urea on nicotine percentage was equivalent to the influence of one-half the same molecular concentration of ammonium salts. 5. Solution cultures, regardless of the form of nitrogen supplied, induced a lower concentration of nicotine in the leaves than did soil cultures even though the dry weights of the leaves were the same. Such an action may have been associated either with differences in the moisture content and aeration of the culture medium or with qualitative or quantitative differences in the salt composition of the culture solutions.

Formation of 2‐(3‐pyridyl)‐pyrrole and 3‐(3‐pyridyl)‐pyrrole by the thermal decomposition of n‐(3‐pyridyl)‐pyrrole

AbstractN‐(3‐Pyridyl)‐pyrrole is converted at 710‐720°into a mixture of 2‐(3‐pyridyl)‐pyrrole, m.p. 100.8°and 3‐ (3‐pyridyl)‐pyrrole, m.p. 137.5°. β‐Nicotyrine was prepared from the pyridylpyrrole melting at 100.8°, in consequence of which the structure of this compound is settled. This same pyridylpyrrole is identical with the compound obtained by Ehrenstein by the dehydrogenation of nornicotine and by Späth by the dehydrogenation of myosmine and l‐nornicotine.The C‐(3‐pyridyl)‐pyrrole, m.p. 72°, which formed the starting material for the synthesis of nicotine by Pictet was not a pure substance but probably a mixture of both isomeric C‐(3‐pyridyl)‐pyrroles.

A New Synthesis of Nornicotine and Nicotine

A New Synthesis of Nornicotine and Nicotine