Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria
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概要
- 論文の詳細を見る
After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (-)-arctigenin (2), (2R,3R)-2-(3',4'-dihydroxy-benzyl)-3-(3",4"-dimethoxybenzyl) butyrolactone (3), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dimethoxybenzyl)- butyrolactone (4), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3"-hydroxy-4"-methoxybenzyl) butyrolactone (5), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dihydroxybenzyl) butyrolactone (6), and (-)-enterolactone (7) by various spectroscopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. Enterolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (-)-(2R,3R) and (+)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferate effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 μM. These results indicate that the transformation of 1 by intestinal flora might be essential for the manifestation of the estrogenic and antiestrogenic activity of 1.
- 社団法人日本薬学会の論文
- 2003-04-01
著者
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NAKAMURA Norio
富山医科薬科大学和漢薬研究所
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Nakamura Norio
Institute Of Natural Medicine University Of Toyama
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HATTORI Masao
Institute of Natural Medicine, University of Toyama
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AKAO Teruaki
Faculty of Pharmaceutical Sciences, University of Toyama
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Akao Teruaki
Faculty Of Pharmaceutical Sciences University Of Toyama
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Akao Teruaki
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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Akao Teruaki
Graduate School Of Medicine And Pharmaceutical Sciences Univ. Of Toyama
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Akao Teruaki
Department Of Enzymatic Physiology Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceuti
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AHN Eun-Mi
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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Xie L‐h
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Uniyersity
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Ahn E‐m
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University
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Ahn Eun-mi
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Universuty
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Abdel‐hafez A
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Uniyersity
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Abdel-hafez Atef
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University:department Of Pharmaceuti
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Nakamura N
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University
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XIE Li-Hua
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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AIIN Eun-Mi
Institute of Natural Medicine, Toyama Medical and Pharmaceutical Uniyersity
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HAFEZ Atef
Institute of Natural Medicine, Toyama Medical and Pharmaceutical Uniyersity
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Hafez Atef
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Uniyersity
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Xie Li-hua
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Uniyersity
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Hattori Masao
Institute Of Natural Medicine Faculty Of Pharmaceutical Sciences
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Akao Teruaki
Institute Of Natural Medicine Toyama Medical
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Nakamura Norio
Institute Of Natural Medicine
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