Hong, Yong-HanYong-HanHongWang, Ssu-ChingSsu-ChingWangHsu, ChinChinHsuLin, Bi-FongBi-FongLinKuo, Yueh-HsiungYueh-HsiungKuoHuang, Ching-JangChing-JangHuang2012-05-122018-07-102012-05-122018-07-10201100218561http://ntur.lib.ntu.edu.tw//handle/246246/239212http://ntur.lib.ntu.edu.tw/bitstream/246246/239212/-1/198.pdfCoumestrol has long been known as the phytoestrogenic compound in alfalfa. However, it has been demonstrated that the ethyl acetate extract of alfalfa sprout (AEA) attenuated the disease severity and increased survival and life span of autoimmune-prone MRL-lpr/lpr mice. Coumestrol, on the contrary, decreased the survival. This study thus aimed to isolate and identify phytoestrogenic compounds other than coumestrol in AEA. AEA was fractionated and separated by successive silica gel chromatography and preparative HPLC. The activity of collected fractions was tracked by a transactivation assay for ERα and ERβ, respectively. In addition to coumestrol, liquiritigenin, isoliquiritigenin, loliolide, and (4S,6S)- and (4R,6S)-4-hydroxy-6- pentadecyltetrahydropyr-2-one were isolated and chemically identified. Except for loliolide, these compounds showed higher transactivation via ERβ than via ERα. The maximal activation via ERα of coumestrol reached 80% that of 1 nM 17β-estradiol (E2), whereas the activations of the remaining five compounds as well as AEA ranged from 8 to 49%. In addition, isoliquiritigenin, loliolide, and (4S,6S)- and (4R,6S)-4-hydroxy-6- pentadecyltetrahydropyr-2-one, but not coumestrol, preferentially inhibited 1 nM E2 induced ERα activation, compared to that ERβ activation. The selectivity of these phytoestrogens might account for the difference between the effects of AEA and coumestrol in autoimmune-prone MRL-lpr/lpr mice observed previously. ? 2010 American Chemical Society.en-US4-hydroxy-6-pentadecyltetrahydropyr-2-one; Alfalfa sprout; isoliquiritigenin; loliolide; phytoestrogen; selective estrogen receptor modulator[SDGs]SDG3[SDGs]SDG124-hydroxy-6-pentadecyltetrahydropyr-2-one; Alfalfa sprout; isoliquiritigenin; loliolide; Phytoestrogenes; Selective estrogen receptor modulators; Chromatography; Esters; High performance liquid chromatography; Silica; Silica gel; Chemical activation; coumestrol; estrogen receptor alpha; estrogen receptor beta; phytoestrogen; plant extract; alfalfa; animal; article; cell line; chemical structure; chemistry; CHO cell; Cricetulus; drug effect; gene expression; genetics; hamster; human; isolation and purification; metabolism; mouse; transcription initiation; Animals; Cell Line; CHO Cells; Coumestrol; Cricetinae; Cricetulus; Estrogen Receptor alpha; Estrogen Receptor beta; Gene Expression; Humans; Medicago sativa; Mice; Molecular Structure; Phytoestrogens; Plant Extracts; Transcriptional Activation; Medicago sativa; Musjournal article10.1021/jf102997p211584492-s2.0-78651071305WOS:000285735200015http://ntur.lib.ntu.edu.tw/bitstream/246246/239212/-1/198.pdf