Quinolizidine alkaloids are

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical syn ...

s that have a

quinolizidine Quinolizidine (norlupinane, octahydro-2''H''-quinolizine) is a nitrogen-containing heterocyclic compound. Some alkaloids (e.g. cytisine and sparteine) are derivatives of quinolizidine. Quinolizidine alkaloids Quinolizidine alkaloids, such as ...

structure; this includes the lupine alkaloids.

Occurrence

Quinolizidine alkaloids can be found in the plant family of

legume A legume () is a plant in the family Fabaceae (or Leguminosae), or the fruit or seed of such a plant. When used as a dry grain, the seed is also called a pulse. Legumes are grown agriculturally, primarily for human consumption, for livestock f ...

s, especially in papilionaceous plants. While the lupine alkaloids (following their name) can be found in lupines, tinctorin, for example, was isolated from the dyer's broom.

Examples

More than 200 quinolizidine alkaloids are known which can be classified into 6 structural types: * the lupinine type with 34 known structures, including lupinine and its derivatives * the camoensine type with 6 known structures, including camoensin * the spartein type with 66 structures, including

sparteine Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in '' Lupinus mutabilis'', and is thought to chelate the bivalent cations calcium and ...

, lupanine, angustifoline * the α-pyridone type with 25 structures, including anagyrine and

cytisine Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as ''Laburnum'' and ''Cytisus'' of the family Fabaceae. It has been used medically to help with smoking cessati ...

* the matrine type with 31 structures, including matrine * and the ormosanin type with 19 structures, including ormosanine.

(–)-Lupinine Structural Formula V2.svg, (–)-lupinine (6R,7S,9S,11S)-(-)-Sparteine Structural Formula V2.svg, (–)-sparteine (6S,7R,9R,11R)-(-)-Lupanine Structural Formula V2.svg, (–)-lupanine (-)-Anagyrine Structural Formula V1.svg, (–)-anagyrine (+)-Matrine Structural Formula V2.svg, (+)-matrine

Properties

Cytisine is the toxic main alkaloid of

laburnum ''Laburnum'', sometimes called golden chain or golden rain, is a genus of two species of small trees in the subfamily Faboideae of the pea family Fabaceae. The species are '' Laburnum anagyroides''—common laburnum and '' Laburnum alpinum''— ...

. Similar to nicotine, it has a stimulating to hallucinogenic effect in low doses and a respiratory paralysing effect in higher doses.

Cytisine Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as ''Laburnum'' and ''Cytisus'' of the family Fabaceae. It has been used medically to help with smoking cessati ...

and matrine are active ingredients of the Sophora beans from Mexico and the cow Seng and Shinkyogan drugs from China and Japan. Quinolizidine alkaloids defend plants against pests and

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s and

breeding Breeding is sexual reproduction that produces offspring, usually animals or plants. It can only occur between a male and a female animal or plant. Breeding may refer to: * Animal husbandry, through selected specimens such as dogs, horses, and ra ...

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, volume=10 , date=2019-10-30 , page=1385 , issn=1664-462X , doi=10.3389/fpls.2019.01385 , s2cid=204938901 , doi-access=free , pmid=31737013 , pmc=6831545 They have various effects on warm-blooded animals and lead to poisoning of grazing livestock (sheep and cattle). Cytisin and anagyrin are particularly responsible for this. The effects of poisoning are stimulation, coordination disorders , shortness of breath, cramps and finally death from respiratory paralysis. Anagyrin acts

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. The only quinolizidine alkaloid used therapeutically is

, which has an antiarrhythmic and labor-promoting effect.

Occurrence

Examples

Properties

References