![Laburnum anagyroides flowering](https://upload.wikimedia.org/wikipedia/commons/8/88/Laburnum_anagyroides_flowering.jpg)
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
disease
A disease is a particular abnormal condition that negatively affects the structure or function of all or part of an organism, and that is not immediately due to any external injury. Diseases are often known to be medical conditions that a ...
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 ...
to reduce QA concentrations lowers these resistances.
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''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 F ...
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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 (Elsevier
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) , volume=100 , issn=0924-2244 , doi=10.1016/j.tifs.2020.03.042 , pages=51–66 , last1=Kaiser , first1=Natalie , last2=Douches , first2=David , last3=Dhingra , first3=Amit , last4=Glenn , first4=Kevin C. , last5=Herzig , first5=Philip Reed , last6=Stowe , first6=Evan C. , last7=Swarup , first7=Shilpa , title=The role of conventional plant breeding in ensuring safe levels of naturally occurring toxins in food crops , date=2020 , s2cid=216391401
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, {{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
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Abstra ...
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* Frontier, areas near or beyond a boundary
Arts and entertainment Music
* ''Frontiers'' (Journey album), 1983
* ''Frontiers'' (Jermaine Jackson album), 1978
* ''Frontiers'' (Jesse Cook album), 2007
* ''Frontiers'' ( ...
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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. The related t ...
. The only quinolizidine alkaloid used therapeutically is
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 ...
,
which has an antiarrhythmic and labor-promoting effect.
References