Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria.

• Xie Li-Hua

  Institute of Natural Medicine, Toyama Medical and Pharmaceutical University

• Ahn Eun-Mi

  Institute of Natural Medicine, Toyama Medical and Pharmaceutical University

• Akao Teruaki

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• Abdel-Hafez Atef Abdel-Monem

  Institute of Natural Medicine, Toyama Medical and Pharmaceutical University

• Nakamura Norio

  Institute of Natural Medicine, Toyama Medical and Pharmaceutical University

• Hattori Masao

  Institute of Natural Medicine, Toyama Medical and Pharmaceutical University

抄録

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.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 51 (4), 378-384, 2003

  公益社団法人 日本薬学会

キーワード

• arctiin
• human intestinal bacteria
• enterolactone
• mammalian lignan
• MCF-7 cell
• phytoestrogen

詳細情報

• CRID: 1390001204163378944
• NII論文ID: 110003615309
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.51.378
• COI: 1:CAS:528:DC%2BD3sXltVejsbc%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 6492243
• PubMed: 12672988
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6492243
• Web Site: http://www.jstage.jst.go.jp/article/cpb/51/4/51_4_378/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2003233785
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可