Diosgenin

Last updated
Diosgenin
Diosgenin.svg
Diosgenina3D.png
Names
IUPAC name
(25R)-Spirost-5-en-3β-ol
Systematic IUPAC name
(2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4′,4a,6a,7-Tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-oxan]-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.396 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-134-3
PubChem CID
UNII
  • InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1 Yes check.svgY
    Key: WQLVFSAGQJTQCK-VKROHFNGSA-N Yes check.svgY
  • InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
    Key: WQLVFSAGQJTQCK-VKROHFNGBS
  • O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)CC6)C
Properties
C27H42O3
Molar mass 414.630 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam species, such as the Kokoro. It is also present in smaller amounts in a number of other species. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.

Contents

Sources

It is present in detectable amounts in Costus speciosus , Smilax menispermoidea , Helicteres isora , species of Paris , Aletris , Trigonella , and Trillium , and in extractable amounts from many species of Dioscorea D. althaeoides , D. colletti , D. composita , [1] D. floribunda , D. futschauensis , D. gracillima , D. hispida , D. hypoglauca , D. mexicana , [2] D. nipponica , D. panthaica , D. parviflora , D. septemloba , and D. zingiberensis . [3]

Industrial uses

Diosgenin is a chemical precursor for several hormones, starting with the Marker degradation process, which includes synthesis of progesterone. [4] The process was used in the early manufacturing of combined oral contraceptive pills. [5] Diosgenin in dietary supplements is not a physiological precursor to estradiol or progesterone, and the use of such products as wild yam has no hormonal activity in the human body. [6]

See also

Related Research Articles

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<span class="mw-page-title-main">Progestogen</span> Steroid hormone that activates the progesterone receptor

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<span class="mw-page-title-main">Yam (vegetable)</span> Edible starchy tuber

Yam is the common name for some plant species in the genus Dioscorea that form edible tubers.

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<i>Dioscorea bulbifera</i> Species of flowering plant in the yam family Dioscoreaceae

Dioscorea bulbifera is a species of true yam in the yam family, Dioscoreaceae. It is native to Africa, Asia and northern Australia. It is widely cultivated and has become naturalized in many regions.

<i>Dioscorea mexicana</i> Species of herbaceous vine

Dioscorea mexicana, Mexican yam or cabeza de negro is a species of yam in the genus Dioscorea.

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Sarsasapogenin is a steroidal sapogenin, that is the aglycosidic portion of a plant saponin. It is named after sarsaparilla, a family of climbing plants found in subtropical regions. It was one of the first sapogenins to be identified, and the first spirostan steroid to be identified as such. The identification of the spirostan structure, with its ketone spiro acetal functionality, was fundamental in the development of the Marker degradation, which allowed the industrial production of progesterone and other sex hormones from plant steroids.

Dioscorea composita, or barbasco, is a species of yam in the genus Dioscorea, native to Mexico. It is notable for its role in the production of diosgenin, which is a precursor for the synthesis of hormones such as progesterone. Russell Marker developed the extraction and manufacture of hormones from D. mexicana at Syntex, starting the trade of D. composita in Mexico. Marker also discovered that the composita variety had a much higher content of diosgenin than the mexicana variety, and therefore it came to replace the latter in the production of synthetic hormones.

<span class="mw-page-title-main">Mexican barbasco trade</span>

The Mexican barbasco trade was the trade of the diosgenin-rich yam species Dioscorea mexicana, Dioscorea floribunda and Dioscorea composita which emerged in Mexico in the 1950s as part of the Mexican steroid industry. The trade consisted in Mexican campesinos harvesting the root in the jungle, selling it to middlemen who brought it to processing plants where the root was fermented and the diosgenin extracted and sold to pharmaceutical companies such as Syntex who used it to produce synthetic hormones.

Dioscorea zingiberensis, is a species of yam, a tuberous root vegetable. It has been cultivated in China for the production of diosgenin, an important pharmaceutical intermediate for the synthesis of steroid hormones. The rhizomes also produces steroidal saponins (TSS) as part of a treatment for cardiovascular disease.

<span class="mw-page-title-main">16-Dehydropregnenolone acetate</span> Chemical compound

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References

  1. "Dioscorea composita". Germplasm Resources Information Network . Agricultural Research Service, United States Department of Agriculture . Retrieved 2008-09-14.
  2. "Dioscorea mexicana". Germplasm Resources Information Network . Agricultural Research Service, United States Department of Agriculture . Retrieved 2008-09-14.
  3. "2950 Diosgenin" . Retrieved 2007-05-29.[ permanent dead link ]
  4. 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.
  5. 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. S2CID   5933910.
  6. Medigović I, Ristić N, Živanović J, Šošić-Jurjević B, Filipović B, Milošević V, Nestorović N “Diosgenin does not express estrogenic activity: a uterotrophic assay” Can J Physiol Pharmacol. 2014 Apr;92(4):292-8. doi: 10.1139/cjpp-2013-0419. Epub 2014 Feb 5. PMID 24708211