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Phytosteroid

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Naturally occurring steroids that are found in plants See also: Phytosterol
Digitoxin, a phytosteroid and cardiac glycoside found in digitalis.

Phytosteroids, also known as plant steroids, are naturally occurring steroids that are found in plants. Examples include digoxin, digitoxin, diosgenin, and guggulsterone, as well as phytosterols like β-sitosterol and other phytoestrogens like isoflavones.

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.

Also in 1940, American chemist Percy Lavon Julian discovered a process to convert a much more abundant phytosteroid -- stigmasterol from soybean -- into progesterone. His process was improved by Padmanabhan Sundararaman and Carl Djerassi in 1977, just as stocks of wild Mexican yam became depleted. Soy stigmasterol soon replaced yam diosgenin as the main starting material for hormone production globally.

References

  1. ^ Hugh 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. Retrieved June 5, 2012.
  3. "Giants of the Past". lipidlibrary.aocs.org. Archived from the 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.
Types of phytochemicals
Terpenoids
Types of terpenes and terpenoids (# of isoprene units)
Basic forms:
  • Acyclic (linear, cis and trans forms)
  • Monocyclic (single ring)
  • Bicyclic (2 rings)
  • Iridoids (cyclopentane ring)
  • Iridoid glycosides (iridoids bound to a sugar)
  • Steroids (4 rings)
Hemiterpenoids (1)
Monoterpenes
(C10H16)(2)
Acyclic
Monocyclic
Bicyclic
Monoterpenoids
(2,modified)
Acyclic
Monocyclic
Bicyclic
Sesquiterpenoids (3)
Diterpenoids (4)
Acyclic
Monocyclic
Bicyclic
Tricyclic
Tetracyclic
Resin acids
Sesterterpenoids (5)
  • Geranylfarnesol
Triterpenoids (6)
Steroids
Other
Sesquarterpenes/oids (7)
  • Ferrugicadiol
  • Tetraprenylcurcumene
Tetraterpenoids
(Carotenoids) (8)
Carotenes
Xanthophylls:
Polyterpenoids (many)
Norisoprenoids (modified)
  • 3-oxo-α-ionol
  • 7,8-dihydroionone
Synthesis
Activated isoprene forms
Phenolic compounds
Types of phenolic compounds
Natural monophenols
Polyphenols
Types of polyphenols
Flavonoids
(C6-C3-C6)
Types of flavonoids
Flavonoids
Anthoxanthins
Flavones
Flavonols
Isoflavones
Neoflavonoids
Flavans
Flavan
Flavan-3-ols
(flavanols)
Flavan-4-ols
(flavanols)
Flavan-3,4-diols
Flavanones
Flavanonols
Anthocyanidins
3-deoxyanthocyanidins
3-hydroxyanthocyanidin
Aurones
Chalcones
Chalcones
Dihydrochalcone
Miscellaneous
Flavonoid biosynthesis
FlavonolignansSilymarin
Lignans
((C6-C3)2)
Stilbenoids
(C6-C2-C6)
CurcuminoidsCurcumin
Tannins
Types of natural tannins
Hydrolysable tannins
Ellagitannins
Gallotannins
Condensed tannins
Phlorotannins
Flavono-ellagitannins
(complex tannins)
Other Miscellaneous
Others
Misc:Polyphenols
Aromatic acids
Aromatic acids
Phenolic acids
Monohydroxybenzoic acids
Aglycones
Glycosides
Dihydroxybenzoic acids
Trihydroxybenzoic acids
Other phenolic acids
Hydroxycinnamic acids
Aromatic amino acids
Phenylethanoids
Others
Misc:
Glucosinolates
Betalains
Chlorophylls
Organic acids
Carbohydrates
Misc:List of phytochemicals and foods in which they are prominent


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