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
别名	(+)-葛雌素
识别
CAS号	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
性质
化学式	C20H22O6
摩尔质量	358.385 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

葛雌素（英語：Miroestrol）是一种植物雌激素，是一种植物模拟雌激素生物活性行为的化学物质。葛雌素于1960年在野葛根（Pueraria mirifica）中分离得到，并认为其是让野葛根重新焕发活力的物质^[1]。最近研究表明重新焕发活力的有效成分可能是其衍生物—去氧葛雌素（deoxymiroestrol），而先前报导的葛雌素可能仅仅存在于分离过程中^[2]，因为去氧葛雌素遇见空气会氧化成葛雌素。

一项关于植物雌激素的雌激素特性的对比研究发现，去氧葛雌素和葛雌素的体外活性和诸如香豆雌酚等植物雌激素相当，且均为17β-雌二醇激动剂^[3]。因为其具有雌激素活性，葛雌素、去氧葛雌素以及相关化合物已经成为有机全合成的目标^[4]^[5]。

含有葛雌素的野葛根提取物被制成膳食补充剂售卖，商家并宣称其具有丰胸的功效。然而由于缺乏确凿证据，美国联邦贸易委员会已对这些未经证实的宣传对营销人员采取法律行动^[6]。

参考文献

^ 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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葛雌素

IUPAC名 (3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^3,12.0^4,9.0^13,18]nonadeca-4,6,8,11-tetraen-14-one
别名	(+)-葛雌素
识别
CAS号	2618-41-9 ^Y
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
性质
化学式	C₂₀H₂₂O₆
摩尔质量	358.385 g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。