Asthma lobelia

Allosedamine 157 is a relatively simple piperidine alkaloid which was isolated more than 60 years ago by Wieland and co-workers from Lobelia inflate. It has good activity against respiratory disorders such as asthma, bronchitis, and pneumonia. The key step of the current synthesis (Scheme 29) is an RCM of enone ester 155 which closes the... 

Lobelia or Indian tobacco consists of the dried leaves and tops of Lobelia inflata (Campanulaceae), an annual herb from the USA and Canada. Lobelia contains about 0.2-0.4% of alkaloids, of which the piperidine derivative lobeline (Figure 6.23) is the chief constituent. Minor alkaloids identified include closely related structures, e.g. lobelanine (Figure 6.23). The North American Indians employed lobelia as an alternative or substitute for tobacco (Nicotiana tabacum Solanaceae), and it is found that lobeline stimulates nicotinic receptor sites in a similar way to nicotine, but with a weaker effect. Lobeline has been employed in preparations intended as smoking deterrents. The crude plant drug has also long been used to relieve asthma and bronchitis, though in large doses it can be quite toxic. 

Lobelia is stated to possess respiratory stimulant, antiasthmatic, antispasmodic, expectorant, and emetic properties. Traditionally, it has been used for bronchitic asthma, chronic bronchitis, and specifically for spasmodic asthma with secondary bronchitis. It is also used topically for myositis and rheumatic nodules. 

Lobelia contains Lobeline and is used in treating asthma. 

Isolates from Indian tobacco (Lobelia inf lata L.), as a crude mixture of bases, have been recognized as expectorants. The same (or similar) fractions were also used both in the treatment of asthma and as emetics. The principal alkaloid in L inflata is lobeline (49), an optically active tertiary amine which, unusual among alkaloids, is reported to readily undergo mutarotation, a process normally associated with sugars. Interestingly, it appears that the aryl-bearing side chains in (49) are derived from phenylalanine (25, R = H) (40). 

Lobelia. Indian tobacco wild tobacco emetic herb asthma wsed bladder pod vomit wort. Dried leaves and tops of Lobelia inflate L., Lobetiaeeae. (The seeds are also used.) Habit. Canada, U.S. ConstiL Leaves and lops chiefly lobeline, also lobelidine, lobelanine, lobelamdine. and other alkaloids. Seeds lobeline, fixed oil. 

Lobelia has been known as an emetic for almost two centuries and has been employed for the relief of asthma for nearly 150 years. 

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. 

Lobelia has long been used by the North American Indians. It was recommended for use in asthma by Cutler in 1813 and was introduced to the English medical... 

L. inflata L. is a traditional medicinal plant native to North America. It contains several piperidine alkaloids. The main alkaloid is lobeline which has a stimulatory effect on the respiratory center and it is applied in the cases of asthma, gas- and narcotic-poisoning. Thus, lobeiine is currently the subject of renewed interest for the treatment of drug abuse and neurological disorders, like Alzheimer s or Parkinson s disease, which pose an important public health problem in industrial countries. As lobeiine can act as a competitive nicotinic receptor antagonist, it is frequently used in antismoking preparations. Interest in Lobelia alkaloids, and in particular (-)-lobeline, the most active of them, has increased in recent years due to their activity on the central nervous system (CNS). 

Allosedamine (113) and (+)-sedamine (119), two piperidine alkaloids isolated from Lobelia inflate, have been used for the treatment of respiratory disorders such as asthma, bronchitis, and pneumonia. While several racemic syntheses have been reported, there are much less asymmetric ones. An enantioselective route to (—)-aUosedamine (113) was developed by Raghaven et al, which commenced with addition of lithium compound 110 to the imine 109 providing the separable aUyUc amine 111 as a 3 1 mixture of diastereoisomers (Scheme 2.27) [45, 46). Six... 

---