2-Lysine Derived Alkaloids

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Presentation transcript:

2-Lysine Derived Alkaloids Piperidine Alkaloids

Lysine Derived Alkaloids As the next homologue to ornithine, lysine and its associated compounds give rise to a number of alkaloids, some of which are analogous to the ornithine group.

LOBELIA Lobelia BHP; BP 1988 (Lobelia Herb, Indian Tobacco) consists of the dried aerial parts of Lobelia inflata (Campanulaceae), an annual herb indigenous to the eastern USA and Canada. It is cultivated in the USA and Holland.

Lobelia inflata Campanulaceae Constituents: Lobelia contains about 0.24-0.4% of alkaloids (BP 1988, not less than 0.25% as determined by a standard stas-Otto procedure) the most important of which is lobeline. Uses: Minor alkaloids identified include closely related structures, e.g. lobelanine . 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.

Biosynthesis of lobeline

Pomegranata The barks, fruit-rind and seeds of the pomegranate, Punica granatum (Punicaceae) all find medicinal use. Both stem and root barks are used and occur in curved or channeled pieces about 5-10cm long and 1-3cm wide. Constituents: They contain about 0.5-0.9% of volatile liquid alkaloids, the chief of which are pelletierine and pseudopelletierine, together with about 22% of tannin. Uses: anthelminthic, Tapeworms, Astringent. Seed extract for use in the treatment of diarrhea, (Antidiarrhoea).

Punica granatum Punicaceae

Chemical composition PELLETIERINE

Piper nigrum The pungency of the fruits of black pepper (Piper nigrum; Piperaceae), a widely used condiment, is mainly due to the piperidine alkaloid Piperine. In this structure, the piperidine ring forms part of a tertiary amide structure, and is incorporated via piperidine itself, the reduction product of Δ1-piperideine

Nicotine, Nicotinic acid & Arecoline 3-Nicotinic Acid Derived Alkaloids Pyridine Alkaloids Nicotine, Nicotinic acid & Arecoline Pyridine Nicotine Tryptophan Nicotinic Acid

PYRIDINE PIPERIDINE ALKALOIDE :

Nicotina Tabacum L.N: Nicotina tabacum F.N: Solanaceae Part used: leaves Use: vermicide

Constituents : I. nicotine II. Anabasine III. Chlorogenic Ac IV. Cafeic Ac V. Nicotinic Ac

N COOH Nicotinic Ac CH=CH─COOH HO Cafeic Ac OH H CH=CH─ C O HO COOH chlorogenic Ac

Biosynthesis of nicotine :

التأثير الضار للتدخين على الصحة و البيئة

أكثر من 1000 مادة سامة تنتج عن احتراق التبغ و 40 منها على الأقل تؤهب لحدوث السرطان

Areka L.N : Areca catechu F.N : palmeae Part Used : fruit extract or juice

Chemical composition: Contains several alkaloids which are reduced pyridine derivatives . CH3 COOCH3 Areclline hydrobromid H N+ Br¯ Use & Dose in veterinary medicine (anti helmentic)

Conium Maculatum L.N: conium maculatum F.N: umbelliferae (apiaceae) Part used: fruit

Chemical composition : coniine , the major alkaloid and conine conceine . Use & Dose antispasmodic / sedative / water hemlock / species / very toxic drug