Glycoalkaloids are a family of chemical compounds derived from

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

s to which

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecul ...

groups are appended. Several are potentially toxic, most notably the

poison A poison is any chemical substance that is harmful or lethal to living organisms. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figurati ...

s commonly found in the plant species '' Solanum dulcamara'' (bittersweet nightshade) and other plants in the genus ''

Solanum ''Solanum'' is a large and diverse genus of flowering plants, which include three food crops of high economic importance: the potato, the tomato and the eggplant (aubergine, brinjal). It is the largest genus in the nightshade family Solana ...

'', including

potato The potato () is a starchy tuberous vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are underground stem tubers of the plant ''Solanum tuberosum'', a perennial in the nightshade famil ...

. A prototypical glycoalkaloid is

solanine Solanine is a glycoalkaloid poison found in species of the Solanaceae, nightshade family within the genus ''Solanum'', such as the potato (''Solanum tuberosum''). It can occur naturally in any part of the plant, including the Leaf, leaves, frui ...

(composed of the sugar solanose and the alkaloid

solanidine Solanidine is a poisonous steroidal alkaloid chemical Chemical compound, compound that occurs in plants of the family Solanaceae, such as potato and ''Solanum americanum''. The sugar portion of glycoalkaloids hydrolyses in the body, leaving the so ...

), which is found in the

. The alkaloidal portion of the glycoalkaloid is also generically referred to as an

aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...

. The intact glycoalkaloid is poorly absorbed from the

gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the Digestion, digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascula ...

, therefore causing gastrointestinal irritation. The aglycone is absorbed and is believed to be responsible for observed nervous system signs.

Taste

Glycoalkaloids are typically bitter tasting, and produce a burning irritation in the back of the

mouth A mouth also referred to as the oral is the body orifice through which many animals ingest food and animal communication#Auditory, vocalize. The body cavity immediately behind the mouth opening, known as the oral cavity (or in Latin), is also t ...

and side of the

tongue The tongue is a Muscle, muscular organ (anatomy), organ in the mouth of a typical tetrapod. It manipulates food for chewing and swallowing as part of the digestive system, digestive process, and is the primary organ of taste. The tongue's upper s ...

. The

Aymara people The Aymara or Aimara (, ) people are an Indigenous people in the Andes and Altiplano regions of South America. Approximately 2.3 million Aymara live in northwest Argentina, Bolivia, Chile, and Peru. The ancestors of the Aymara lived in the reg ...

Bolivia Bolivia, officially the Plurinational State of Bolivia, is a landlocked country located in central South America. The country features diverse geography, including vast Amazonian plains, tropical lowlands, mountains, the Gran Chaco Province, w ...

use taste to detect the levels of glycoalkaloids in potatoes to determine the safety of various cultigens.

Detection

Although not routinely available, detection of alkaloids in tissues or urine is possible for laboratory diagnosis of exposure.

Treatment

Sale of a glycoalkaloid-based treatment marketed by Lane Labs USA Inc. for prevention of

skin cancer Skin cancers are cancers that arise from the Human skin, skin. They are due to the development of abnormal cells (biology), cells that have the ability to invade or metastasis, spread to other parts of the body. It occurs when skin cells grow ...

was banned by the FDA in 2004 as an unapproved

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

.fda.gov, news item 1086

References

External links

*{{Commons category-inline Alkaloids found in Solanaceae