Nicotiana Anabasine, Myosmine, Nicotine

Tobacco use is primarily due to psychopharmacological effects of nicotine (Henningfleld et al. 2006). Nicotine is a tobacco alkaloid, a basic substance that contains a cychc nitrogenous nucleus. In Nicotiana plants, most alkaloids are 3-pyridyl derivatives In cured leaf of Maryland Robinson Medium Broadleaf, 24 pyridine derivatives were identified, including nicotine, nomicotine, anabasine, oxynicotine, myosmine, 3-acetylpyridine, 2,3 -dipyridyl, iticotinamide, anatabine, nicotinic acid, and unidentified pyridine alkaloids of derivatives thereof (Tso 1990). Nicotine is the principal alkaloid in commercial tobacco (this was confirmed in 34 out of 65 Nicotiana species) nomicotine, rather than nicotine, appears to be the main alkaloid in 19 out of 65 species and anabasine is the third most important. In addition to the above-mentioned principal and minor alkaloids, the presence of many trace amounts of new alkaloids or their derivatives were frequently reported, including, for example, 2.4 -dipyridyl, 4,4 -dipyridyl, N -formylanabasine, A -formylanatabine, N -acetylanatabine, N -hexanoyl-nomicotine, N -octanoyl-nomicotine, T-(6-hydroxyoctanoyl) nomicotine, and l -(7-hydroxyoctanoyl) nor-nicotine. 

Over sixty species of Nicotiana exist that produce nicotine alkaloids (nicotine, nornicotine, anatabine, anabasine). Nicotine is the predominant alkaloid in over 50% of the Nicotiana species. Nornicotine is the major alkaloid in about 30% to 40% of Nicotiana species. Anabasine and anatabine are not usually the principal alkaloids in Nicotiana (17B05). Tobaccos that accumulate and have high levels of alkaloids tend to also have accumulations of minor alkaloids, for example, cotinine, myosmine, nicotyrine, 2,3 -bipyridine, and numerous derivatives of the major alkaloids, for example, alkyl, acyl, and nitroso derivatives of nicotine and the other... 

Desmodiurntriflorum Nicotine (44 R = Me), nornicotine (44 R = H),anabasine (45), and two unidentified alkaloids have been isolated from Nicotiana noctiflora. Confirmation that myosmine (46) is true alkaloid in various Nicotiana species and not a decomposition product of nicotine has been obtained." Anabasine (45) has also been found in Verbascum songaricum. ... 

Cestroideae. Nomicotine (major alkaloid), nicotine, and anabasine were detected in Salpiglossis sinuata (Salpiglossis clade) (Schroter 1958, 1963). The same alkaloids were found as constituents of Streptosolen jamesonii (BrowaUieae clade) (Schroter 1963). Nicotine and its nor congener were isolated also from the leaves of Cestrum diurnum and C. nocturnum (Cestreae clade), in addition cotinine and myosmine from the latter species only. This was the first report on the occurrence of cotinine and myosmine outside of the genus Nicotiana. However, all these alkaloids were present in such small concentrations that the toxicity attributed to both Cestrum species should be based on different constituents (steroidal saponins, see Sect. 7.7) (Halim et al. 1971). 

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