Diosgenin
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| Names | |
|---|---|
| IUPAC name
(3β,25R)-spirost-5-en-3-ol | |
| Identifiers | |
512-04-9  | |
| ChEBI | CHEBI:4629  |
| ChEMBL | ChEMBL412437 |
| ChemSpider | 89870 |
| EC Number | 208-134-3 |
| Jmol interactive 3D | Image |
| PubChem | 99474 |
| UNII | K49P2K8WLX |
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| 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). | |
| verify (what is ?) | |
| 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]
Diosgenin may behave as a prodrug to progesterone.[7][8]
References
- ↑ "Dioscorea mexicana information". Germplasm Resources Information Network (GRIN). United States Department of Agriculture. Retrieved 2008-09-14.
- ↑ "2950 Diosgenin". Retrieved 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:10.1021/ja01869a023.
- ↑ 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.
- ↑ 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.
- ↑ Cayen MN, Dvornik D (1979). "Effect of diosgenin on lipid metabolism in rats" (abstract page). J. Lipid Res. 20 (2): 162–74. PMID 438658.
- ↑ 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.
- ↑ 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.
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External links
- Diosgenin at the US National Library of Medicine Medical Subject Headings (MeSH)
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