Miroestrol

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
Other names
(+)-Miroestrol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • InChI=1S/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1 ☒N
    Key: RJKLDOLOCIQYFS-PRTISISMSA-N ☒N
  • InChI=1/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1
    Key: RJKLDOLOCIQYFS-PRTISISMBT
  • CC1([C@@H]2C3=C(C=C(C=C3)O)OC=C2[C@]4([C@H]5C1CC([C@@H]5O)(CC4=O)O)O)C
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).
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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.

Chemical structure of deoxymiroestrol

A comparative study of the estrogenic properties of phytoestrogens found that both deoxymiroestrol and miroestrol were comparable in activity in vitro to other known phytoestrogens such as coumestrol as 17β-oestradiol agonists.[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 a lack of conclusive evidence for such claims. The Federal Trade Commission has taken legal action against marketers for these unproven claims.[6]

  1. ^ Cain, J. C. (1960). "Miroestrol - An Estrogen from the Plant Pueraria mirifica". Nature. 188 (4753): 774–777. doi:10.1038/188774a0. PMID 13689829. S2CID 4154375.
  2. ^ 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.
  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. S2CID 25341363.
  4. ^ 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.
  5. ^ 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.
  6. ^ "Federal Trade Commission v. Vital Dynamics" (PDF). FTC. 26 December 2002.