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 s ...

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 Legumes are plants in the pea family Fabaceae (or Leguminosae), or the fruit or seeds of such plants. When used as a dry grain for human consumption, the seeds are also called pulses. Legumes are grown agriculturally, primarily for human consum ...

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 ''Genista tinctoria'', the dyer's greenweed or dyer's broom, is a species of flowering plant in the family Fabaceae. Its other common names include dyer's whin, waxen woad and waxen wood. The Latin specific epithet ''tinctoria'' means "used as a ...

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 Lupinine is a quinolizidine alkaloid present in the genus ''Lupinus'' (colloquially referred to as lupins) of the flowering plant family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound as ...

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 and 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 metals calcium a ...

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

anagyrine Anagyrine is a teratogenic alkaloid first isolated from (and named for) ''Anagyris foetida'' in the year 1885 by French biologists Hardy and Gallois. ''A. foetida'' (family Fabaceae), the Stinking Bean Trefoil, is a highly toxic shrub native to th ...

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 cessa ...

* the matrine type with 31 structures, including

matrine Matrine is an alkaloid found in plants from the family ''Fabaceae''. It has a variety of pharmacological effects, including in-vitro anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism. Matrine possesses strong antitumor a ...

* 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 cessa ...

and

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

disease A disease is a particular abnormal condition that adversely affects the structure or function (biology), function of all or part of an organism and is not immediately due to any external injury. Diseases are often known to be medical condi ...

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 rab ...

to reduce QA concentrations lowers these resistances. {{Unbulleted list citebundle , {{cite journal , journal=

Trends in Food Science and Technology ''Trends in Food Science and Technology'' is a monthly peer-reviewed review journal covering food science and technology. It is an official publication of the European Federation of Food Science and Technology and of the International Union of Fo ...

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EFSA The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002 ...

IUFoST The International Union of Food Science and Technology (IUFoST) ( ) is the global scientific organization and voice for food science and technology representing more than 300,000 food scientists, engineers and technologists through its work in m ...

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Elsevier Elsevier ( ) is a Dutch academic publishing company specializing in scientific, technical, and medical content. Its products include journals such as ''The Lancet'', ''Cell (journal), Cell'', the ScienceDirect collection of electronic journals, ...

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, date=2021 , isbn=978-0-12-819195-8 , oclc=1225947369 , pages=xxi+756 , doi=10.1016/c2018-0-05018-5 , s2cid=243013936{{rp, pages=430–450 , {{cite journal , last1=Gulisano , first1=Agata , last2=Alves , first2=Sofia , last3=Martins , first3=João Neves , last4=Trindade , first4=Luisa M. , title=Genetics and Breeding of ''Lupinus mutabilis'': An Emerging Protein Crop , journal=

Frontiers in Plant Science ''Frontiers in Plant Science'' is a peer-reviewed scientific journal covering all aspects of botany. It was established in 2010 and is published by Frontiers Media. The editor-in-chief is Yunde Zhao (University of California, San Diego). Abstract ...

, publisher= Frontiers , 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

teratogenic Teratology is the study of abnormalities of physiological development in organisms during their life span. It is a sub-discipline in medical genetics which focuses on the classification of congenital abnormalities in dysmorphology caused by ...

. The only quinolizidine alkaloid used therapeutically is

, which has an antiarrhythmic and labor-promoting effect.

Occurrence

Examples

Properties

References