葛雌素

葛雌素
	IUPAC名; (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
別名	(+)-葛雌素
識別
CAS號	2618-41-9
PubChem	165001
ChemSpider	144658
SMILES	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;
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;
InChIKey	RJKLDOLOCIQYFS-PRTISISMBT
KEGG	C08831
性質
化學式	C20H22O6
摩爾質量	358.385 g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

葛雌素（英語：Miroestrol）是一種植物雌激素，是一種植物模擬雌激素生物活性行為的化學物質。葛雌素於1960年在野葛根（Pueraria mirifica）中分離得到，並認為其是讓野葛根重新煥發活力的物質^[1]。最近研究表明重新煥發活力的有效成分可能是其衍生物—去氧葛雌素（deoxymiroestrol），而先前報導的葛雌素可能僅僅存在於分離過程中^[2]，因為去氧葛雌素遇見空氣會氧化成葛雌素。

一項關於植物雌激素的雌激素特性的對比研究發現，去氧葛雌素和葛雌素的體外活性和諸如香豆雌酚等植物雌激素相當，且均為17β-雌二醇激動劑^[3]。因為其具有雌激素活性，葛雌素、去氧葛雌素以及相關化合物已經成為有機全合成的目標^[4]^[5]。

含有葛雌素的野葛根提取物被製成膳食補充劑售賣，商家並宣稱其具有豐胸的功效。然而由於缺乏確鑿證據，美國聯邦貿易委員會已對這些未經證實的宣傳對營銷人員採取法律行動^[6]。

參考文獻

^ Cain, J. C. Miroestrol - An Estrogen from the Plant Pueraria mirifica. Nature. 1960, 188 (4753): 774–777. PMID 13689829. S2CID 4154375. doi:10.1038/188774a0.
^ Chansakaow, S.; Ishikawa, T.; Seki, H.; Sekine, K.; Okada, M.; Chaichantipyuth, C. Identification of Deoxymiroestrol as the Actual Rejuvenating Principle of "Kwao Keur", Pueraria mirifica. The Known Miroestrol may be an Artifact. Journal of Natural Products. 2000, 63 (2): 173–175. PMID 10691701. doi:10.1021/np990547v.
^ Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. Comparative Study of Estrogenic Properties of eight Phytoestrogens in MCF7 Human Breast Cancer Cells. Journal of Steroid Biochemistry and Molecular Biology. 2005, 94 (5): 431–443. PMID 15876408. S2CID 25341363. doi:10.1016/j.jsbmb.2004.12.041.
^ Corey, E. J.; Wu, L. I. Enantioselective Total Synthesis of Miroestrol. Journal of the American Chemical Society. 1993, 115 (20): 9327–9328. doi:10.1021/ja00073a074.
^ Ito, F.; Kumamoto, T.; Yamaguchi, K.; Ishikawa, T. 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. 2009, 65 (4): 771–785. doi:10.1016/j.tet.2008.11.055.
^ Federal Trade Commission v. Vital Dynamics (PDF). FTC. 26 December 2002.

[1] Cain, J. C. Miroestrol - An Estrogen from the Plant Pueraria mirifica. Nature. 1960, 188 (4753): 774–777. PMID 13689829. S2CID 4154375. doi:10.1038/188774a0.

[2] Chansakaow, S.; Ishikawa, T.; Seki, H.; Sekine, K.; Okada, M.; Chaichantipyuth, C. Identification of Deoxymiroestrol as the Actual Rejuvenating Principle of "Kwao Keur", Pueraria mirifica. The Known Miroestrol may be an Artifact. Journal of Natural Products. 2000, 63 (2): 173–175. PMID 10691701. doi:10.1021/np990547v.

[3] Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. Comparative Study of Estrogenic Properties of eight Phytoestrogens in MCF7 Human Breast Cancer Cells. Journal of Steroid Biochemistry and Molecular Biology. 2005, 94 (5): 431–443. PMID 15876408. S2CID 25341363. doi:10.1016/j.jsbmb.2004.12.041.

[4] Corey, E. J.; Wu, L. I. Enantioselective Total Synthesis of Miroestrol. Journal of the American Chemical Society. 1993, 115 (20): 9327–9328. doi:10.1021/ja00073a074.

[5] Ito, F.; Kumamoto, T.; Yamaguchi, K.; Ishikawa, T. 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. 2009, 65 (4): 771–785. doi:10.1016/j.tet.2008.11.055.

[6] Federal Trade Commission v. Vital Dynamics (PDF). FTC. 26 December 2002.

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