Glycoalkaloids are a family of chemical compounds derived from

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of simila ...

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, fructose, and galactose. Compound sugars, also called disaccharides or do ...

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

poison Poison is a chemical substance that has a detrimental effect to life. 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 figuratively, with a broa ...

s commonly found in the plant species ''

Solanum dulcamara ''Solanum dulcamara'' is a species of vine in the genus '' Solanum'' (which also includes the potato and the tomato) of the family Solanaceae. Common names include bittersweet, bittersweet nightshade, bitter nightshade, blue bindweed, Amara Dul ...

'' (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 Solanaceae ...

'', including

potato The potato is a starchy food, a tuber of the plant ''Solanum tuberosum'' and is a root vegetable native to the Americas. The plant is a perennial in the nightshade family Solanaceae. Wild potato species can be found from the southern Uni ...

. A prototypical glycoalkaloid is

solanine Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus '' Solanum'', such as the potato (''Solanum tuberosum''), the tomato (''Solanum lycopersicum''), and the eggplant (''Solanum melongena''). It can occ ...

(composed of the sugar solanose and the alkaloid solanidine), 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 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 molecule. Detection A way to identify aglycone ...

. 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 digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans and ...

but causes gastrointestinal irritation. The aglycone is absorbed and is believed to be responsible for observed nervous system signs. Glycoalkaloids are typically bitter tasting, and produce a burning irritation in the back of the

mouth In animal anatomy, the mouth, also known as the oral cavity, or in Latin cavum oris, is the opening through which many animals take in food and issue vocal sounds. It is also the cavity lying at the upper end of the alimentary canal, bounded on ...

and side of the

tongue The tongue is a muscular organ in the mouth of a typical tetrapod. It manipulates food for mastication and swallowing as part of the digestive process, and is the primary organ of taste. The tongue's upper surface (dorsum) is covered by taste ...

. The

Aymara people Aymara may refer to: Languages and people * Aymaran languages, the second most widespread Andean language ** Aymara language, the main language within that family ** Central Aymara, the other surviving branch of the Aymara(n) family, which today ...

Bolivia , image_flag = Bandera de Bolivia (Estado).svg , flag_alt = Horizontal tricolor (red, yellow, and green from top to bottom) with the coat of arms of Bolivia in the center , flag_alt2 = 7 × 7 square p ...

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

cultigens A cultigen () or cultivated plant is a plant that has been deliberately altered or selected by humans; it is the result of artificial selection. These plants, for the most part, have commercial value in horticulture, agriculture or forestry. Beca ...

. Although not routinely available, detection of alkaloids in tissues or urine is possible for laboratory diagnosis of exposure. 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 skin. They are due to the development of abnormal cells that have the ability to invade or spread to other parts of the body. There are three main types of skin cancers: basal-cell skin cancer (BCC) ...

was banned by the FDA in 2004 as an unapproved

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhala ...

.fda.gov, news item 1086

References

External links

*{{Commons category-inline Alkaloids found in Solanaceae