Glycoalkaloid

Glycoalkaloids are a family of chemical compounds derived from alkaloids to which sugar groups are appended. Several are potentially toxic, most notably the poisons commonly found in the plant species Solanum dulcamara (bittersweet nightshade) and other plants in the genus Solanum, including potato.

Chemical structure of α-solanine distinguishing the sugar (solatriose moiety) and the alkaloid (solanidine moiety) portions

A prototypical glycoalkaloid is solanine (composed of the sugar solanose and the alkaloid solanidine), which is found in potato. The alkaloidal portion of the glycoalkaloid is also generically referred to as an aglycone. The intact glycoalkaloid is poorly absorbed from the gastrointestinal tract 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 and side of the tongue. The Aymara people of Bolivia use taste to detect the levels of glycoalkaloids in potatoes to determine the safety of various cultigens.[1]

Although not routinely available, detection of alkaloids in tissues or urine is possible for laboratory diagnosis of exposure.[2]

Sale of a glycoalkaloid-based treatment marketed by Lane Labs USA Inc. for prevention of skin cancer was banned by the FDA in 2004 as an unapproved drug.[3]

References
  1. Johns, T., Keen, S.L. (1986). "Taste evaluation of potato glycoalkaloids by the Aymara: A case study in human chemical ecology". Human Ecology. 14 (4): 437–452. CiteSeerX 10.1.1.1026.9058. doi:10.1007/bf00888308.CS1 maint: multiple names: authors list (link)
  2. http://cal.vet.upenn.edu/poison/plants/ppeurop.htm Archived June 16, 2007, at the Wayback Machine
  3. fda.gov, news item 1086 Archived October 7, 2006, at the Wayback Machine
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.