Diosgenin
From Wikipedia, the free encyclopedia
| Diosgenin | |
|---|---|
 |
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| IUPAC name | (3β,25R)-spirost-5-en-3-ol |
| Identifiers | |
| CAS number | [512-04-9] |
| PubChem | |
| SMILES | CC1CCC2(C(C3C(O2)CC4C3(CCC5 C4CC=C6C5(CCC(C6)O)C)C)C)OC1 |
| Properties | |
| Molecular formula | C27H42O3 |
| Molar mass | 414.62058 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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. The sugar-free, aglycone, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products. It is present in Costus speciosus, Smilax menispermoidea, species of Paris, Trigonella, and Trillium, and many species of Dioscorea - D. althaeoides, colletti, futschauensis, gracillima, hispida, hypoglauca, nipponica, panthaica, parviflora, septemloba, and zingiberensis.[1]
[edit] Clinical Uses
Diosgenin is the precursor for the semisynthesis of progesterone[2] which in turn was used in early combined oral contraceptive pills.
The unmodified steroid has estrogenic activity[3] and can reduce the level of serum cholesterol.[4]
[edit] References
- ^ 2950 Diosgenin. Retrieved on 2007-05-29.
- ^ 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:.
- ^ 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:. PMID 15372201.
- ^ Cayen MN, Dvornik D (1979). "Effect of diosgenin on lipid metabolism in rats" (abstract page). J. Lipid Res. 20 (2): 162–74. PMID 438658.
