Estrogenic and Anti-estrogenic Activities of Cassia tora Phenolic Constituents
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- El-Halawany Ali Mahmoud
- Institute of Natural Medicine, University of Toyama
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- Chung Mi Hwa
- Institute of Natural Medicine, University of Toyama
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- Nakamura Norio
- Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts
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- Ma Chao-Mei
- Institute of Natural Medicine, University of Toyama
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- Nishihara Tsutomu
- Faculty of Pharmaceutical Sciences, Hyogo College of Medicine
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- Hattori Masao
- Institute of Natural Medicine, University of Toyama
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Through an estrogenic activity bioassay-guided fractionation of the 70% ethanolic extract of Cassia tora seeds two new phenolic triglucosides, torachrysone 8-O-[β-D-glucopyranosyl(1→3)-O-β-D-glucopyranosyl(1→6)-O-β-D-glucopyranoside] (1) and toralactone 9-O-[β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside] (2), along with seven known compounds were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidence. The estrogenic activity of the fractions and the isolated compounds were investigated using the estrogen-dependent proliferation of MCF-7 cells. In addition, the yeast two hybrid assay expressing estrogen receptor α (ERα) and β (ERβ) and the ERα competitor screening assay (ligand binding screen) were used to verify the binding affinities of the isolated compounds to ER. Furthermore, a naringinase pre-treatment of the 70% alcoholic extract of Cassia tora seeds resulted in a significant increase in its estrogenic activity. From the naringinase pre-treated extract six compounds were isolated, among which 6-hydroxymusizin and aurantio-obtusin showed the most potent estrogenic activity, while torachrysone, rubrofusarin and toralactone showed a significant anti-estrogenic activity. Finally, the structure requirements responsible for the estrogenic activity of the isolated compounds were studied by investigating the activity of several synthetic compounds and chemically modifying the isolated compounds. The basic nucleus 1,3,8-trihyroxynaphthalene (T3HN) was found to play a principal role in the binding affinity of these compounds to ER.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 55 (10), 1476-1482, 2007
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679147623552
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- NII論文ID
- 110006404696
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 8918877
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可