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| Diosgenin | |
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| IUPAC name | (3β,25R)-spirost-5-en-3-ol |
| Identifiers | |
| CAS number | [512-04-9] |
| PubChem | |
| SMILES |
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| 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 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.
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Sources
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, mexicana[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
- ^ "Dioscorea mexicana information". Germplasm Resources Information Network (GRIN). United States Department of Agriculture. Retrieved on 2008-09-14.
- ^ "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:
- ^ Djerassi C (1992), "Steroid research at Syntex: "the pill" and cortisone", Steroids 57(12): 631–41, doi:, PMID 1481227
- ^ 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, <http://www.jlr.org/cgi/content/abstract/20/2/162>
External links
Wikipedia content modification information:
- This page was last modified on 14 September 2008, at 15:19.
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