Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria.
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- Xie Li-Hua
- Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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- Ahn Eun-Mi
- Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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- Akao Teruaki
- Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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- Abdel-Hafez Atef Abdel-Monem
- Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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- Nakamura Norio
- Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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- Hattori Masao
- Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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Abstract
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′-dihydroxybenzyl)-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 proliferative 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.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 51 (4), 378-384, 2003
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204163378944
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- NII Article ID
- 110003615309
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- NII Book ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD3sXltVejsbc%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6492243
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- PubMed
- 12672988
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed