Solasodine
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Solasodine is a
poisonous 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 ...
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 similar ...
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
that occurs in plants of the family
Solanaceae The Solanaceae , or nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and orn ...
such as potatoes and tomatoes.
Solasonine Solasonine is a glycoalkaloid that is found in Solanum plants of the family Solanaceae. Solasonine is a poisonous chemical compound when used at high levels. It is a glycoside of solasodine Solasodine is a poisonous alkaloid chemical compound ...
and
solamargine Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from '' Solanum nigrum'' fungal endophyte ''Aspergillus flavus''. It is a glycoalk ...
are
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) ...
derivatives of solasodine. Solasodine is
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 ...
to hamster fetuses in a dose of 1200 to 1600 mg/kg. Literature survey reveals that solasodine has diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and various effects on central nervous system.


Uses

It is commercially used as a precursor for the production of complex
steroidal A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and ...
compounds such as
contraceptive pill Oral contraceptives, abbreviated OCPs, also known as birth control pills, are medications taken by mouth for the purpose of birth control. Female Two types of female oral contraceptive pill, taken once per day, are widely available: * The combin ...
s, via a 16-DPA intermediate.


See also

* ''
Solanum mauritianum ''Solanum mauritianum'' is a small tree or shrub native to South America, including Northern Argentina, Southern Brazil, Paraguay and Uruguay. Its common names include earleaf nightshade (or "ear-leaved nightshade"), woolly nightshade, flannel we ...
''


References

Steroidal alkaloids Plant toxins Steroidal alkaloids found in Solanaceae Spiro compounds {{alkaloid-stub