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

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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.

収録刊行物

  • Chemical & pharmaceutical bulletin   [巻号一覧]

    Chemical & pharmaceutical bulletin 51(4), 378-384, 2003-04-01  [この号の目次]

    公益社団法人日本薬学会

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各種コード

  • NII論文ID(NAID)
    110003615309
  • NII書誌ID(NCID)
    AA00602100
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092363
  • NDL 記事登録ID
    6492243
  • NDL 雑誌分類
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-D167
  • データ提供元
    CJP書誌  CJP引用  NDL  NII-ELS  J-STAGE 
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