Diosgenin

Diosgenin
Names
IUPAC name
(3β,25R)-spirost-5-en-3-ol
Identifiers
512-04-9 Yes
ChEBI CHEBI:4629 
ChEMBL ChEMBL412437 Yes
ChemSpider 89870 Yes
EC number 208-134-3
Jmol-3D images Image
PubChem 99474
UNII K49P2K8WLX Yes
Properties
Molecular formula
 C27H42O3
Molar mass 414.62 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Diosgenin, a steroid 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

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

Diosgenin is the precursor for the semisynthesis of 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]

References

  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.
  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.


External links