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Phytosteroid

From Wikipedia, the free encyclopedia
Naturally occurring steroids that are found in plants
See also:Phytosterol
Digitoxin, a phytosteroid andcardiac glycoside found indigitalis.

Phytosteroids, also known asplant steroids, arenaturally occurringsteroids that are found inplants.[1] Examples includedigoxin,digitoxin,diosgenin, andguggulsterone, as well asphytosterols[a] likeβ-sitosterol.[1]

Industrial use

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Steroid pharmaceuticals that are identical or similar to humansteroid 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 chemistRussell Earl Marker developed the process known asMarker degradation, which convertsdiosgenin from MexicanDioscorea yams into16-dehydropregnenolone acetate, which has a four-ring structure and can be used to synthesize commonly used steroid hormones. Marker's process reduced the price ofprogesterone from $80/gram in early 1944 to $2/gram in 1951.[2]

Also in 1940, American chemistPercy Lavon Julian discovered a process to convert a much more abundant phytosteroid --stigmasterol fromsoybean -- into progesterone. Stigmasterol is a byproduct of soybean oil refinement.[3] His process was improved byPadmanabhan Sundararaman andCarl Djerassi in 1977, just as stocks of wild Mexican yam became depleted.[4] Soy stigmasterol soon replaced yam diosgenin as the main starting material for hormone production globally.[5]

References

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  1. ^The relationship between phytosteroids and phytosterols is akin to the relationship between steroids andsterols: the latter is a subset of the former, specifically those with ahydroxyl group at the 3-position.
  1. ^abHugh L. J. Makin; D.B. Gower; B. Kirk (29 June 2013).Steroid Analysis. Springer Science & Business Media. pp. 621–.ISBN 978-94-017-3078-5.
  2. ^"Russell Marker and the Mexican Steroid Hormone Industry".American Chemical Society. RetrievedJune 5, 2012.
  3. ^"Giants of the Past". lipidlibrary.aocs.org. Archived fromthe original on 15 April 2012.
  4. ^Sundararaman P, Djerassi C (October 1977). "A convenient synthesis of progesterone from stigmasterol".The Journal of Organic Chemistry.42 (22):3633–4.doi:10.1021/jo00442a044.PMID 915584.
  5. ^Soto Laveaga, Gabriela (2009).Jungle Laboratories: Mexican peasants, National Projects and the Making of the Pill. Duke University.ISBN 9780822346050.
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