Diosgenin

Diosgenin
Diosgenin
IUPAC name
(3β,25R)-spirost-5-en-3-ol
Identifiers
CAS number 512-04-9 YesY
PubChem 99474
ChemSpider 89870 YesY
UNII K49P2K8WLX YesY
EC number 208-134-3
ChEMBL CHEMBL412437 YesY
Jmol-3D images Image 1
Properties
Molecular formula C27H42O3
Molar mass 414.62 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Contents

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]

Chemistry

Main article: Marker degradation

The glycoside dioscin from the Mexican wild yam root, Dioscorea, constituted the first plant source for steroid drugs.

Hydrolysis of this saponin leads to scission of the trisaccharide at the 3-position and the formation of the aglycone, diosgenin. Treatment of this acetal with hot acetic anhydride in the presence of toluenesulfonic acid leads initially to protonation of one of the acetal oxygens followed by elimination to form an enol ether. Oxidation by means of chromium trioxide leads to preferential attack at the electron-rich enol ether double bond. In effect, this transformation converts the side chain at C-17 in diosgenin to the acetyl group required for many steroid drugs. Heating that intermediate in with alcoholic sodium hydroxide leads to the elimination of the ester grouping beta to the ketone; there is thus obtained 16-dehydropregnenolone acetate. The presence of the olefin at C-17 allows ready entry to C-19 androstanes and provides the necessary function for the synthesis of potent C-16- and C-16,17-substituted corticosteroids.

Diosgenin Synthesis.png

Marker, Russell E.; Wagner, R. B.; Ulshafer, Paul R.; Wittbecker, Emerson L.; Goldsmith, Dale P. J.; Ruof, Clarence H. (1947). "Steroidal sapogenins". Journal of the American Chemical Society 69 (9): 2167–2230. doi:10.1021/ja01201a032. PMID 20262743. 

References

  1. ^ "Dioscorea mexicana information". Germplasm Resources Information Network (GRIN). United States Department of Agriculture. http://www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl?14226. Retrieved 2008-09-14. 
  2. ^ "2950 Diosgenin". http://tcm.cambridgesoft.com/tcm/showcompound.asp?monograph=2950&formgroup=basenp_form_group&dbname=TCM&formmode=edit. 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. http://www.jlr.org/cgi/content/abstract/20/2/162. 

External links


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Look at other dictionaries:

  • diosgenin — [dī΄əz jen′in; dī äz′jə nin΄] n. a steroid, C27H42O3, found in yams and used to synthesize various hormones, as progesterone …   English World dictionary

  • diosgenin — /duy oz jen in, duy oz jeuh nin/, n. Biochem. a crystalline compound, C27H42O3, the aglycone of dioscin: used in the synthesis of steroidal hormones, as of progesterone. [ < G Diosgenin (1936), equiv to NL Dios(corea) the yam genus from which it… …   Universalium

  • diosgenin — diosgeninas statusas T sritis chemija apibrėžtis Steroidinis augalinis glikozidas. atitikmenys: angl. diosgenin rus. диосгенин …   Chemijos terminų aiškinamasis žodynas

  • diosgenin — noun A steroid sapogenin, obtained from certain yams, that has estrogenic activity …   Wiktionary

  • diosgenin — The aglycon of dioscing a sapogenin derived from the saponins dioscin and trillin found in the roots of plants such as the yam; its steroid portion serves as a source from which pregnenolone and progesterone can be prepared. * * * di·os·gen·in… …   Medical dictionary

  • Diosgenin — Di|os|ge|nin [nlat. Dioscorea = Jams (Bot.); ↑ genin], das; s; Syn.: (25R) Spirost 5 en 3ß ol: ein in Jamswurzeln als Glykosid (Dioscin, ↑ Saponin) mit 2 Molekülen Rhamnose u. 1 Molekül Glucose vorliegendes …   Universal-Lexikon

  • diosgenin — n. synthetic female hormone …   English contemporary dictionary

  • diosgenin — [dʌɪ ɒsdʒənɪn] noun Chemistry a steroid compound obtained from Mexican yams and used in the synthesis of steroid hormones. Origin 1930s: from dios (from the mod. L. genus name Dioscorea) + genin, denoting steroids that occur as the non sugar part …   English new terms dictionary

  • diosgenin — di·os·gen·in …   English syllables

  • diosgenin — ˌdīˌäzˈjenə̇n, dīˈäzjən noun ( s) Etymology: dios (from New Latin Dioscorea) + genin : a crystalline steroid sapogenin C27H42O3 obtained chiefly in Mexico from locally available yams and used as a starting material for the synthesis of steroid… …   Useful english dictionary

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