Nicotinoids - Nicotine-related Natural Products

Nornicotine and anabasine count amongthe minor alkaloids of tobacco. Whereas Nkotiana species contain the (S)-nornicotine, Duboisia hopwoodii produces the (J )-enantiomer. Anabasine is with up to 2.6% the principal alkaloid of Anabasis aphylla. The anabasine content in Nkotiana glauca is comparatively high and reaches 1 %. [Pg.490]

There is a whole range of natural products, which are not just structurally related to nicotine, but also with regard to their pharmacological activity. Of these, only lobeline, (-)-epibatidine, (-)-cytisine and (+)-anatoxin A will be discussed [Pg.491]

210 Duboisia hopwoodii (a), Nicotiana glauca (b) and Lobelia inflata (c). [Pg.491]

211 Nicotine-related alkaloids from dart-poison frogs, laburnum and cyanobacteria. [Pg.491]

Indian tobacco (Lobelia inflata), also known as pukeweed , has been used for centuries by the Penobscots people in the Northeastern United States and the Canadian Maritimes, as an entheogenic and emetic drug, before Samuel Thompson (1769-1843), an herbalist from New Hampshire, claimed it as a valuable remedy. The roots were used for the treatment of sexually transmitted diseases, e.g. syphilis, and skin diseases were medicated with poultices from smashed leaves. By parenteral application, Indian tobacco is effective against oedema and asthma. Thus, Lobelia inflata was found since 1820 in many pharmacopoeias. [Pg.491]

Many pesticides are not as novel as they may seem. Some, such as the pyre-throid and neonicotinoid insecticides, are modeled on natural insecticides. Synthetic pyrethroids are related to the natural pyrethrins (see Chapter 12), whereas the neo-nicotinoids share structural features with nicotine. In both cases, the synthetic compounds have the same mode of action as the natural products they resemble. Also, the synthetic pyrethroids are subject to similar mechanisms of metabolic detoxication as natural pyrethrins (Chapter 12). More widely, many detoxication mechanisms are relatively nonspecific, operating against a wide range of compounds that... [Pg.3]

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