Diosgenin

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Diosgenin
Diosgenin.svg
Diosgenina3D.png
Names
IUPAC name
(3β,25R)-spirost-5-en-3-ol
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.396
EC Number 208-134-3
UNII
Properties
C27H42O3
Molar mass 414.63 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone), diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.

Sources[edit]

It is present in Costus speciosus, Smilax menispermoidea, species of Paris, Aletris, Trigonella, and Trillium, and many species of Dioscorea - D. althaeoides, colletti, futschauensis, gracillima, hispida, hypoglauca, floribunda, mexicana and composita[1] nipponica, panthaica, parviflora, septemloba, and zingiberensis.[2]

Clinical uses[edit]

Diosgenin is a precursor for several hormones, starting with the Marker degradation process. This includes progesterone[3] which in turn was used in early combined oral contraceptive pills.[4] The unmodified steroid has estrogenic activity[5] and can reduce the level of serum cholesterol.[6]

Diosgenin may behave as a prodrug to progesterone.[7][8]

References[edit]

  1. ^ "Dioscorea mexicana information". Germplasm Resources Information Network (GRIN). United States Department of Agriculture. Retrieved 2008-09-14. 
  2. ^ "2950 Diosgenin". Retrieved 2007-05-29. [permanent dead link]
  3. ^ Marker RE, Krueger J (1940). "Sterols. CXII. Sapogenins. XLI. The Preparation of Trillin and its Conversion to Progesterone". J. Am. Chem. Soc. 62 (12): 3349–3350. doi:10.1021/ja01869a023. 
  4. ^ Djerassi C (December 1992). "Steroid research at Syntex: "the pill" and cortisone". Steroids. 57 (12): 631–41. doi:10.1016/0039-128X(92)90016-3. PMID 1481227. 
  5. ^ Liu MJ, Wang Z, Ju Y, Wong RN, Wu QY (2005). "Diosgenin induces cell cycle arrest and apoptosis in human leukemia K562 cells with the disruption of Ca2+ homeostasis". Cancer Chemother. Pharmacol. 55 (1): 79–90. doi:10.1007/s00280-004-0849-3. PMID 15372201. 
  6. ^ Cayen MN, Dvornik D (1979). "Effect of diosgenin on lipid metabolism in rats" (abstract page). J. Lipid Res. 20 (2): 162–74. PMID 438658. 
  7. ^ Tucci M, Benghuzzi H (2003). "Structural changes in the kidney associated with ovariectomy and diosgenin replacement therapy in adult female rats". Biomed Sci Instrum. 39: 341–6. PMID 12724917. 
  8. ^ Hajirahimkhan, Atieh; Dietz, Birgit; Bolton, Judy (2013). "Botanical Modulation of Menopausal Symptoms: Mechanisms of Action?". Planta Medica. 79 (07): 538–553. doi:10.1055/s-0032-1328187. ISSN 0032-0943. PMC 3800090Freely accessible. PMID 23408273. 

External links[edit]

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