{{Short description|Naturally occurring steroids that are found in plants}} {{See also|Phytosterol}} [[File:Digitoxin structure.svg|thumb|225px|right|class=skin-invert-image|Digitoxin, a phytosteroid and cardiac glycoside found in digitalis.]]
'''Phytosteroids''', also known as '''plant steroids''', are naturally occurring steroids that are found in plants.<ref name="MakinGower2013">{{cite book|author1=Hugh L. J. Makin|author2=D.B. Gower|author3=B. Kirk|title=Steroid Analysis|url=https://books.google.com/books?id=EKbuCAAAQBAJ&pg=PA621|date=29 June 2013|publisher=Springer Science & Business Media|isbn=978-94-017-3078-5|pages=621–}}</ref> Examples include digoxin, digitoxin, diosgenin, and guggulsterone, as well as phytosterols{{efn|The relationship between phytosteroids and phytosterols is akin to the relationship between steroids and sterols: the latter is a subset of the former, specifically those with a hydroxyl group at the 3-position.}} like β-sitosterol.<ref name="MakinGower2013" />
== Industrial use == Steroid pharmaceuticals that are identical or similar to human steroid hormones are very widely used in medicine. However, the four-ring structure of a steroid is quite expensive to replicate using direct synthetic methods.
In 1938–1940, American chemist Russell Earl Marker developed the process known as Marker degradation, which converts diosgenin from Mexican ''Dioscorea'' yams into 16-dehydropregnenolone acetate, which has a four-ring structure and can be used to synthesize commonly used steroid hormones. Marker's process reduced the price of progesterone from $80/gram in early 1944 to $2/gram in 1951.<ref name="Marker Degradation: Creation of the Mexican Steroid Hormone Industry">{{cite web|title=Russell Marker and the Mexican Steroid Hormone Industry|url=https://www.acs.org/content/acs/en/education/whatischemistry/landmarks/progesteronesynthesis.html|publisher=American Chemical Society|accessdate=June 5, 2012}}</ref>
Also in 1940, American chemist Percy Lavon Julian discovered a process to convert a much more abundant phytosteroid -- stigmasterol from soybean -- into progesterone. Stigmasterol is a byproduct of soybean oil refinement.<ref>{{cite web | url = http://lipidlibrary.aocs.org/history/Julian/index.htm | title = Giants of the Past | publisher = lipidlibrary.aocs.org | url-status = dead | archive-url = https://web.archive.org/web/20120415001340/http://lipidlibrary.aocs.org/history/Julian/index.htm | archive-date = 15 April 2012 }}</ref> His process was improved by Padmanabhan Sundararaman and Carl Djerassi in 1977, just as stocks of wild Mexican yam became depleted.<ref>{{cite journal | vauthors = Sundararaman P, Djerassi C | title = A convenient synthesis of progesterone from stigmasterol | journal = The Journal of Organic Chemistry | volume = 42 | issue = 22 | pages = 3633–4 | date = October 1977 | pmid = 915584 | doi = 10.1021/jo00442a044 }}</ref> Soy stigmasterol soon replaced yam diosgenin as the main starting material for hormone production globally.<ref name="Sotowholebook">{{cite book|author=Soto Laveaga, Gabriela|year=2009|title=Jungle Laboratories: Mexican peasants, National Projects and the Making of the Pill |publisher=Duke University |isbn=9780822346050 |url=https://books.google.com/books?id=TRvzw39OccwC}}</ref>
==References== {{notelist}} {{Reflist|25em}}
{{Phytochemical}} {{Authority control}}
Category:Steroids
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