Lignan enterolactone

Fig. 2.86. Chemical structures of the iosflavones daidzein, genistein, O-desmethylangolensin, equol, and the lignans enterolactone and enterodiol. Reprinted with permission from Z. Kuklenyik el al. [209].

Jacobs, E., Kulling, S.E., and Metzler, M., Novel metabolites of the mammalian lignans enterolactone and enterodiol in human urine, J. Steroid Biochem. Mol Biol, 68, 211, 1999. 

Heinonen, S., Nurmi, T., Liukkonen, K., Poutanen, K., Wahala, K., Deyama, T., Nishibe, S., and Adlercreutz, H., In vitro metabolism of plant lignans new precursors of mammalian lignans enterolactone and enterodiol, J. Agric. Food Chem., 49, 3178, 2001. 

Bannwart C, Adlercreutz H, Fotsis T, Wahala K, Hase T, Brunow G. 1984. Identification of o-desmethylangolensin, a metabolite of daidzein and of matairesinol, one likely plant precursor of the animal lignan enterolactone in human urine. Finn Chem Lett 4-5 120-125. 

Adlercreutz H, Fotsis T, Heikkinen R, Dwyer JT, Woods M, Goldin BR, Gorbach SL. 1982. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Lancet 2 1295-1299. 

Power, K.A., Saarinen, N.M., Chen, J., and Thompson, L.U. 2004. Lignans (enterolactone and enterodiol) negate the proliferative effect of sioflavone (genistein) on MCF-7 breast cancer cells in vitro and in vivo (abstract). Proc. AACR 45, 878. 

The development of a novel h ten for radioimmunoassay of the lignan, enterolactone in plasma (serum) was accomplished by T. Makela et al. The essay utilized enterolactone derivatives that have a carboxylic acid moiety for the production of antiserum and tracer. The preparation of (+)-frans-5-carboxytrimethylenoxyenterolactone utilized the Reimer-Tiemann reaction for the formyiation of 2-benzyloxyphenol. 

Makela, T., Matikainen, J., Wahala, K., Hase, T. Development of a novel hapten for radioimmunoassay of the lignan, enterolactone in plasma (serum). Total synthesis of ( )-trans-5-carboxymethoxyenterolactone and several analogues. Tetrahedron 2000, 56,1873-1882. 

S Heinonen, T Nurmi, K Liukkonen, K Potanen, K Wahala, T Deyama, S Nishibe, Adlercreutz. In Vitro Metabolism of plant bgnans New precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem 49 3178-3186, 2001. 

Enterolactone had been described as a moderate competitive inhibitor of human estrogen synthetase (aromatase) and it binds to or near the substrate region of the active site of the P-450 enzyme [61], In another study [89], seven lignans were evaluated for their abilities to inhibit aromatase enzyme activity in a human preadipose cell culture system. The lignan enterolactone and its precursors, didemethoxymatairesinol and 3 -demethoxy-3-<9-demethylmatairesinol, decreased aromatase enzyme activity, with Ki values... 

FIGURE 25.1 Structures of nonsteroidal phytoestrogens. The most prevalent classes of phytoestrogens are (1) flavones apigenin (2) kaempferol (3) isoflavones daidzein (4) genistein (5) formononetin (6) biochanin A (7) lignans enterolactone (8) coumestans coumestrol (9) flavanones 8-prenylnaringenin. 

MAHALANABIS, K.K., M. MUMTAZ, V. SNIECKUS. 1982. Dimetalated tertiary succinamides Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Lett. 23 3975. 

Lignans Enterolactone, enterolactone Estrogen agonists and antagonists, inhibit tyrosine kinase Flax seed, rye... 

The lignan phytoestrogen precursors matairesinol and secisolariciresinol are present in foods as glycosides and are converted by gut bacteria to the two main mammalian lignans enterolactone and entero-diol, respectively, which are weakly oestrogenic. Matairesinol undergoes dehydroxylation and demethylation directly to enterolactone, whereas secisolariciresinol is converted to enterodiol, which can then be oxidized to enterolactone. After absorption, enterolactone and enterodiol are converted to their yS-glucuronides and eventually excreted in urine. 

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