Enterolactone (ENL) and enterodiol (END) are found in high concentrations i
n human body fluids after ingestion of flaxseed and whole-grain products. A
lthough much interest is presently focused on these mammalian lignans becau
se of their putative beneficial health effects, little is known about their
metabolic fate in humans. We have now identified nine novel metabolites of
ENL and END in the urine of female and male humans ingesting flaxseed for
five days. The chemical structures of six ENL metabolites and of three END
metabolites were elucidated by GC/MS analysis and comparison with authentic
reference compounds obtained by chemical synthesis. The six identified met
abolites of ENL were the products of monohydroxylation at the para-position
and at both ortho-positions of the parent hydroxy group of either aromatic
ring. Likewise, the three END metabolites were formed through aromatic mon
ohydroxylation at the para- and ortho-positions. The biological significanc
e of these metabolites remains to be established. (C) 1999 Elsevier Science
Ltd. All rights reserved.