Miroestrol
| |
| Names | |
|---|---|
| IUPAC name
(3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.03,12.04,9.013,18]nonadeca-4,6,8,11-tetraen-14-one
| |
| Systematic IUPAC name
(3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.03,12.04,9.013,18]nonadeca-4,6,8,11-tetraen-14-one | |
| Other names
(+)-Miroestrol; Mirestrol
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| KEGG | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C20H22O6 | |
| Molar mass | 358.385 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Miroestrol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroestrol was first reportedly isolated from the Thai herb Pueraria mirifica in 1960 and thought to be responsible for the supposed rejuvenating properties of the plant.[1] However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol (shown below), and the reported presence of miroestrol may only have been an artifact of the isolation procedure.[2] When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.
A comparative study of the estrogenic properties of phytoestrogens found that both deoxymiroestrol and miroestrol were comparable in activity than other known phytoestrogens such as coumestrol.[3] Because of their estrogenic activities, miroestrol, deoxymiroestrol, and other related compounds have been the targets of scientific research including total synthesis.[4][5]
Extracts of Pueraria mirifica reportedly containing miroestrol are marketed as dietary supplements intended to lead to breast enhancement in women. However, there is no scientific basis for such claims. The Federal Trade Commission has taken legal action against marketers for these fraudulent claims.[6]
While Pueraria Mirifica has not been proven to enhance breast development in women. The size of a women's breast is closely linked to estrogen levels, and given that Pueraria Mirifica seems to have a similar estrogenic effect to that of Premarin (Concentrated Equine Estrogen) it is promising as a potential herbal breast enhancement. As well as potentially having uses in Hormone Therapy. More testing is required to give a better understanding of it's exact effects. [7]
References
- ^ Cain, J. C. (1960). "Miroestrol - An Estrogen from the Plant Pueraria mirifica". Nature. 188 (4753): 774–777. doi:10.1038/188774a0. PMID 13689829.
- ^ Chansakaow, S.; Ishikawa, T.; Seki, H.; Sekine, K.; Okada, M.; Chaichantipyuth, C. (2000). "Identification of Deoxymiroestrol as the Actual Rejuvenating Principle of "Kwao Keur", Pueraria mirifica. The Known Miroestrol may be an Artifact". Journal of Natural Products. 63 (2): 173–175. doi:10.1021/np990547v. PMID 10691701.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. (2005). "Comparative Study of Estrogenic Properties of eight Phytoestrogens in MCF7 Human Breast Cancer Cells". Journal of Steroid Biochemistry and Molecular Biology. 94 (5): 431–443. doi:10.1016/j.jsbmb.2004.12.041. PMID 15876408.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Corey, E. J.; Wu, L. I. (1993). "Enantioselective Total Synthesis of Miroestrol". Journal of the American Chemical Society. 115 (20): 9327–9328. doi:10.1021/ja00073a074.
- ^ Ito, F.; Kumamoto, T.; Yamaguchi, K.; Ishikawa, T. (2009). "Synthetic Studies toward Miroestrols: Trials for Elongation of the Methyl Group of 5-Substituted 2-Methyl-2-Cyclohexanone to 3-Methyl-2-Butenyl Function". Tetrahedron. 65 (4): 771–785. doi:10.1016/j.tet.2008.11.055.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ "Federal Trade Commission v. Vital Dynamics" (PDF). FTC.
- ^ "Efficacy comparison of Pueraria mirifica (PM) against conjugated equine estrogen (CEE) with/without medroxyprogesterone acetate (MPA) in the treatment of climacteric symptoms in perimenopausal women: phase III study". J Med Assoc Thai.