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Chemical Compound Review

Enterodiol     (2S,3S)-2,3-bis[(3- hydroxyphenyl)methyl]bu...

Synonyms: Arbo 9, CHEMBL471076, SureCN120183, CCRIS 8460, HMDB05056, ...
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Disease relevance of Enterodiol


High impact information on Enterodiol


Chemical compound and disease context of Enterodiol


Biological context of Enterodiol

  • Apoptosis analysis by the terminal deoxynucleotidyl transferase-mediated dUTP nick end labeling assay showed an increased percentage of apoptotic cells in the floating cells after enterodiol alone or combined treatments [8].
  • However, the rate of hydrolysis in plasma was significantly slower than that in urine for all analytes except enterodiol, for which the reverse was true [9].

Anatomical context of Enterodiol


Associations of Enterodiol with other chemical compounds

  • SDG is metabolized by the colonic microflora to the mammalian lignans enterodiol (END) and enterolactone (ENL), and was hypothesized to reduce plasma lipid concentrations and improve antioxidant capacity [12].
  • Smaller decreases in aromatase activity were observed with the lignan, enterodiol (End) and its theoretical precursors, O-demethylsecoisolariciresinol (ODSI), demethoxysecoisolariciresinol (DMSI) and didemethylsecoisolariciresinol (DDSI) [13].

Gene context of Enterodiol


Analytical, diagnostic and therapeutic context of Enterodiol

  • Lignans are a widely distributed class of natural products, whose functions and distribution suggest that they are one of the earliest forms of defense to have evolved in vascular plants; some, such as podophyllotoxin and enterodiol, have important roles in cancer chemotherapy and prevention, respectively [16].
  • Plasma enterodiol and enterolactone concentrations were measured by liquid chromatography with tandem mass spectrometry [2].


  1. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Adlercreutz, H., Fotsis, T., Heikkinen, R., Dwyer, J.T., Woods, M., Goldin, B.R., Gorbach, S.L. Lancet (1982) [Pubmed]
  2. Plasma enterolignans are associated with lower colorectal adenoma risk. Kuijsten, A., Arts, I.C., Hollman, P.C., van't Veer, P., Kampman, E. Cancer Epidemiol. Biomarkers Prev. (2006) [Pubmed]
  3. Dietary lignins are precursors of mammalian lignans in rats. Begum, A.N., Nicolle, C., Mila, I., Lapierre, C., Nagano, K., Fukushima, K., Heinonen, S.M., Adlercreutz, H., Rémésy, C., Scalbert, A. J. Nutr. (2004) [Pubmed]
  4. Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese diet. Adlercreutz, H., Honjo, H., Higashi, A., Fotsis, T., Hämäläinen, E., Hasegawa, T., Okada, H. Am. J. Clin. Nutr. (1991) [Pubmed]
  5. Mammalian lignans enterolactone and enterodiol, alone and in combination with the isoflavone genistein, do not promote the growth of MCF-7 xenografts in ovariectomized athymic nude mice. Power, K.A., Saarinen, N.M., Chen, J.M., Thompson, L.U. Int. J. Cancer (2006) [Pubmed]
  6. Genistein alone and in combination with the mammalian lignans enterolactone and enterodiol induce estrogenic effects on bone and uterus in a postmenopausal breast cancer mouse model. Power, K.A., Ward, W.E., Chen, J.M., Saarinen, N.M., Thompson, L.U. Bone (2006) [Pubmed]
  7. Reliability of serum measurements of lignans and isoflavonoid phytoestrogens over a two-year period. Zeleniuch-Jacquotte, A., Adlercreutz, H., Akhmedkhanov, A., Toniolo, P. Cancer Epidemiol. Biomarkers Prev. (1998) [Pubmed]
  8. Lignans are involved in the antitumor activity of wheat bran in colon cancer SW480 cells. Qu, H., Madl, R.L., Takemoto, D.J., Baybutt, R.C., Wang, W. J. Nutr. (2005) [Pubmed]
  9. Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. Taylor, J.I., Grace, P.B., Bingham, S.A. Anal. Biochem. (2005) [Pubmed]
  10. Uptake and metabolism of enterolactone and enterodiol by human colon epithelial cells. Jansen, G.H., Arts, I.C., Nielen, M.W., Müller, M., Hollman, P.C., Keijer, J. Arch. Biochem. Biophys. (2005) [Pubmed]
  11. Suitability of a batch in vitro fermentation model using human faecal microbiota for prediction of conversion of flaxseed lignans to enterolactone with reference to an in vivo rat model. Aura, A.M., Oikarinen, S., Mutanen, M., Heinonen, S.M., Adlercreutz, H.C., Virtanen, H., Poutanen, K.S. European journal of nutrition. (2006) [Pubmed]
  12. A lignan complex isolated from flaxseed does not affect plasma lipid concentrations or antioxidant capacity in healthy postmenopausal women. Hallund, J., Ravn-Haren, G., Bügel, S., Tholstrup, T., Tetens, I. J. Nutr. (2006) [Pubmed]
  13. Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes. Wang, C., Mäkelä, T., Hase, T., Adlercreutz, H., Kurzer, M.S. J. Steroid Biochem. Mol. Biol. (1994) [Pubmed]
  14. Synthesis of enterolactone and enterodiol precursors as potential inhibitors of human estrogen synthetase (aromatase). Mäkelä, T.H., Wähälä, K.T., Hase, T.A. Steroids (2000) [Pubmed]
  15. Hydroxymatairesinol, a novel enterolactone precursor with antitumor properties from coniferous tree (Picea abies). Saarinen, N.M., Wärri, A., Mäkelä, S.I., Eckerman, C., Reunanen, M., Ahotupa, M., Salmi, S.M., Franke, A.A., Kangas, L., Santti, R. Nutrition and cancer. (2000) [Pubmed]
  16. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. Dinkova-Kostova, A.T., Gang, D.R., Davin, L.B., Bedgar, D.L., Chu, A., Lewis, N.G. J. Biol. Chem. (1996) [Pubmed]
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