Document Detail

Uptake and metabolism of enterolactone and enterodiol by human colon epithelial cells.
MedLine Citation:
PMID:  15680909     Owner:  NLM     Status:  MEDLINE    
The enterolignans enterolactone and enterodiol are phytoestrogens that are formed from plant lignans by microorganisms in the human colon. Enterolignans circulate in plasma as conjugates. We hypothesized that conjugation of enterolignans takes place in colon epithelial cells, and studied the time course of uptake and metabolism of enterolactone and enterodiol in three human colon epithelial cell lines. In addition, the conjugates were identified by mass spectrometry with accurate mass measurement (LC/QTOFMS/MS). Intracellular levels of conjugated enterolactone and enterodiol in HT29 cells rose immediately after starting the exposure. This was accompanied by a rapid decrease in free enterolactone and enterodiol in the exposure medium of HT29 and (un)differentiated CaCo-2 but not of CCD841CoTr cells. Conjugation and excretion of enterolactone and enterodiol was complete within 8 h, except for enterodiol in CaCo-2 cells ( approximately 48 h). Enterolactone appears to be more rapidly metabolized and/or excreted than enterodiol, and also the appearance of conjugated enterolactone in medium is less affected by the presence of enterodiol than vice versa. Total (free plus conjugated) enterolignan concentrations remained constant throughout the experiments. Three conjugates were identified in exposure medium of HT29 cells: enterolactone-sulfate, enterolactone-glucuronide, and enterodiol-glucuronide. Taken together, our data suggest that phase II metabolism of enterolactone and enterodiol already may take place during uptake in the colon and that colon epithelial cells may be responsible for this metabolism.
Guus H E Jansen; Ilja C W Arts; Michel W F Nielen; Michael Müller; Peter C H Hollman; Jaap Keijer
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Archives of biochemistry and biophysics     Volume:  435     ISSN:  0003-9861     ISO Abbreviation:  Arch. Biochem. Biophys.     Publication Date:  2005 Mar 
Date Detail:
Created Date:  2005-01-31     Completed Date:  2005-04-05     Revised Date:  2009-11-03    
Medline Journal Info:
Nlm Unique ID:  0372430     Medline TA:  Arch Biochem Biophys     Country:  United States    
Other Details:
Languages:  eng     Pagination:  74-82     Citation Subset:  IM    
RIKILT-Institute of Food Safety, Wageningen, The Netherlands.
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MeSH Terms
4-Butyrolactone / analogs & derivatives*,  metabolism*
Caco-2 Cells
Cell Line
Colon / metabolism*,  pathology
HT29 Cells
Intestinal Mucosa / metabolism*
Lignans / metabolism*
Metabolic Clearance Rate
Reg. No./Substance:
0/Lignans; 76543-15-2/2,3-bis(3'-hydroxybenzyl)butyrolactone; 76543-16-3/2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; 96-48-0/4-Butyrolactone

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