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'''Miroesterol''' is a [[phytoestrogen]], a plant-derived chemical that mimics the biological activity of the hormone [[estrogen]]. Miroesterol 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.<ref>{{cite journal | title = Miroesterol-estrogen from the plant Pueraria mirifica | author = Cain, James C. | journal = Nature | year = 1960 | volume = 188 | pages = 774–7 | doi = 10.1038/188774a0 | pmid = 13689829}}</ref> 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.<ref>{{cite journal | author = Chansakaow, Sunee; Ishikawa, Tsutomu; Seki, Hiroko; Sekine, Keiko; Okada, Mineaki; Chaichantipyuth, Chaiyo | title = Identification of deoxymiroestrol as the actual rejuvenating principle of "Kwao Keur", Pueraria mirifica. The known miroestrol may be an artifact | journal = Journal of Natural Products | year = 2000 | volume = 63 | issue = 2 | pages = 173–175 | doi = 10.1021/np990547v | pmid = 10691701}}</ref> When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.
'''Miroesterol''' is a [[phytoestrogen]], a plant-derived chemical that mimics the biological activity of the hormone [[estrogen]]. Miroesterol 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.<ref>{{cite journal | title = Miroesterol-estrogen from the plant Pueraria mirifica | author = Cain, James C. | journal = Nature | year = 1960 | volume = 188 | pages = 774–7 | doi = 10.1038/188774a0 | pmid = 13689829}}</ref> 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.<ref>{{cite journal | author = Chansakaow, Sunee; Ishikawa, Tsutomu; Seki, Hiroko; Sekine, Keiko; Okada, Mineaki; Chaichantipyuth, Chaiyo | title = Identification of deoxymiroestrol as the actual rejuvenating principle of "Kwao Keur", Pueraria mirifica. The known miroestrol may be an artifact | journal = Journal of Natural Products | year = 2000 | volume = 63 | issue = 2 | pages = 173–175 | doi = 10.1021/np990547v | pmid = 10691701}}</ref> 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 deoxymiroestrol was similar in activity to other known phytoestrogens, such as [[coumestrol]], but that miroestrol was significantly less active.<ref>{{cite journal | title = Comparative study of estrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells | author = Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. | journal = Journal of Steroid Biochemistry and Molecular Biology |year = 2005 | volume = 94 | issue = 5 | pages = 431–443 | doi = 10.1016/j.jsbmb.2004.12.041 | pmid = 15876408}}</ref> Because of their estrogenic activities, miroestrol, deoxymiroestrol, and other related compounds have been the targets of scientific research including [[total synthesis]].<ref>{{cite journal | author = [[Elias James Corey|Corey, E. J.]]; Wu, Laurence I. | title = Enantioselective total synthesis of miroestrol | journal = [[Journal of the American Chemical Society]] | year = 1993 | volume = 115 | issue = 20 | pages = 9327–8 | doi = 10.1021/ja00073a074}}</ref><ref>{{cite journal | author = Ito, Fumihiro; Kumamoto, Takuya; Yamaguchi, Kentaro; Ishikawa, Tsutomu | title = Synthetic studies toward miroestrols: trials for elongation of the methyl group of 5-substituted 2-methyl-2-cyclohexanone to 3-methyl-2-butenyl function | journal = Tetrahedron | year = 2009 | volume = 65 | issue = 4 | pages = 771–785 | doi = 10.1016/j.tet.2008.11.055}}</ref>
A comparative study of the estrogenic properties of phytoestrogens found that deoxymiroesterol was similar in activity to other known phytoestrogens, such as [[coumesterol]], but that miroesterol was significantly less active.<ref>{{cite journal | title = Comparative study of estrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells | author = Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. | journal = Journal of Steroid Biochemistry and Molecular Biology |year = 2005 | volume = 94 | issue = 5 | pages = 431–443 | doi = 10.1016/j.jsbmb.2004.12.041 | pmid = 15876408}}</ref> Because of their estrogenic activities, miroesterol, deoxymiroesterol, and other related compounds have been the targets of scientific research including [[total synthesis]].<ref>{{cite journal | author = [[Elias James Corey|Corey, E. J.]]; Wu, Laurence I. | title = Enantioselective total synthesis of miroestrol | journal = [[Journal of the American Chemical Society]] | year = 1993 | volume = 115 | issue = 20 | pages = 9327–8 | doi = 10.1021/ja00073a074}}</ref><ref>{{cite journal | author = Ito, Fumihiro; Kumamoto, Takuya; Yamaguchi, Kentaro; Ishikawa, Tsutomu | title = Synthetic studies toward miroestrols: trials for elongation of the methyl group of 5-substituted 2-methyl-2-cyclohexanone to 3-methyl-2-butenyl function | journal = Tetrahedron | year = 2009 | volume = 65 | issue = 4 | pages = 771–785 | doi = 10.1016/j.tet.2008.11.055}}</ref>


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.<ref>For example, ''[http://www.ftc.gov/os/2002/12/vdicmp.pdf Federal Trade Commission v. Vital Dynamics]''</ref>
Extracts of ''[[Pueraria mirifica]]'' reportedly containing miroesterol 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.<ref>For example, ''[http://www.ftc.gov/os/2002/12/vdicmp.pdf Federal Trade Commission v. Vital Dynamics]''</ref>


[[File:Deoxymiroestrol.png|thumb|left|Chemical structure of deoxymiroestrol]]{{clear-left}}
[[File:Deoxymiroesterol.png|thumb|left|Chemical structure of deoxymiroesterol]]{{clear-left}}


==References==
==References==

Revision as of 20:10, 18 August 2010

Miroestrol
Names
Other names
(+)-Miroesterol; Miresterol
Identifiers
3D model (JSmol)
  • O=C4C[C@@]5(O)[C@H](O)[C@]3([H])[C@@](C5)([H])C(C)(C)[C@]2([H])C1=CC=C(O)C=C1OC=C2[C@@]34O
Properties
C20H22O6
Molar mass 358.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Miroesterol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroesterol 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 deoxymiroesterol was similar in activity to other known phytoestrogens, such as coumesterol, but that miroesterol was significantly less active.[3] Because of their estrogenic activities, miroesterol, deoxymiroesterol, and other related compounds have been the targets of scientific research including total synthesis.[4][5]

Extracts of Pueraria mirifica reportedly containing miroesterol 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]

File:Deoxymiroesterol.png
Chemical structure of deoxymiroesterol

References

  1. ^ Cain, James C. (1960). "Miroesterol-estrogen from the plant Pueraria mirifica". Nature. 188: 774–7. doi:10.1038/188774a0. PMID 13689829.
  2. ^ Chansakaow, Sunee; Ishikawa, Tsutomu; Seki, Hiroko; Sekine, Keiko; Okada, Mineaki; Chaichantipyuth, Chaiyo (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)
  3. ^ 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)
  4. ^ Corey, E. J.; Wu, Laurence I. (1993). "Enantioselective total synthesis of miroestrol". Journal of the American Chemical Society. 115 (20): 9327–8. doi:10.1021/ja00073a074.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Ito, Fumihiro; Kumamoto, Takuya; Yamaguchi, Kentaro; Ishikawa, Tsutomu (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)
  6. ^ For example, Federal Trade Commission v. Vital Dynamics
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