Whole Sesame Seed Is as Rich a Source of Mammalian Lignan Precursors as Whole Flaxseed
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The mammalian lignans enterolactone and enterodiol, which are produced by the microflora in the colon of humans and animals from precursors in foods, have been suggested to have potential anticancer effects. This study determined the production of mammalian lignans from precursors in food bars containing 25 g unground whole flaxseed (FB), sesame seed (SB), or their combination (FSB; 12.5 g each). In a randomized crossover study, healthy postmenopausal women supplemented their diets with the bars for 4 wk each separated by 4-wk washout periods, and urinary mammalian lignan excretion was measured at baseline and after 4 wk as a marker of mammalian lignan production. Results showed an increase with all treatments (65.1-81.0 mumol/day; P < 0.0001), which did not differ among treatments. Lignan excretion with the whole flaxseed was similar to results of other studies using ground flaxseed. An unidentified lignan metabolite was detected after consumption of SB and FSB but not of FB. Thus, we demonstrated for the first time that 1) precursors from unground whole flaxseed and sesame seed are converted by the bacterial flora in the colon to mammalian lignans and 2) sesame seed, alone and in combination with flaxseed, produces mammalian lignans equivalent to those obtained from flaxseed alone.Keywords:
Enterolactone
Crossover study
The dietary origin of lignan phytoestrogens is still poorly understood more than 20 years after their discovery in human urine. Their level in urine has been associated with the consumption of dietary fiber. This paper reports the study of the excretion of enterolactone, assayed by a time-resolved fluoroimmunoassay, in rats fed a diet supplemented with 15% wheat bran, one of the main sources of fiber in Western countries. Enterolactone excretion regularly increased during the two weeks of the diet to reach a value of 45 nmol/day. The level of excretion also increased upon preadaptation to ferulic acid, structurally related to secoisolariciresinol, an established precursor of enterolactone in flaxseeds, and decreased upon preadaptation to potato starch rich in fiber. These results show that the formation of lignans from wheat bran is influenced by the diet, possibly because of an adaptation of the colonic microflora.
Enterolactone
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Our previous studies demonstrated that lignan metabolites, enterolactone and enterodiol, inhibited colonic cancer cell growth by inducing cell cycle arrest and apoptosis. This study is focused on the cancer preventive impact of lignan secoisolariciresinol diglucoside (SDG), one of the prominent lignan glycoside, in human colonic cancer SW480 cells. Treatment with SDG at 0–40 μmol/L for 48 hrs resulted in a dose- and time-dependent decrease in cell numbers, which was comparable to enterolactone. These cell growth inhibitions by SDG were not mediated by cytotoxicity, but rather linked to an increased cell cycle arrest at S-phase. Furthermore, HPLC analysis indicated SDG in the media for 48 hrs was much more stable than enterolactone (stability at 95% for SDG in comparison to 57% for enterolactone). The intracellular levels of SDG rather than enterolactone were undetectable, suggesting that SDG was not readily absorbed or metabolized to its metabolites in this short-term cell culture system. Taken together, these findings provide novel characteristics of dietary lignan precursor on colonic cancer growth inhibition and may enhance our understanding of bioavailability of dietary lignans for cancer prevention (supported by USDA Cooperative Project KS 680-0199184).
Enterolactone
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Phytoestrogens occur naturally in plants and are structurally similar to mammalian estrogens. The lignans are a class of phytoestrogen and can be metabolized to the biologically active enterolignans, enterodiol, and enterolactone by a consortium of intestinal bacteria. Secoisolariciresinol diglucoside (SDG), a plant lignan, is metabolized to enterodiol and, subsequently, enterolactone. Matairesinol, another plant lignan, is metabolized to enterolactone. Other dietary enterolignan precursors include lariciresinol, pinoresinol, syringaresinol, arctigenin, and sesamin. Enterolignan exposure is determined in part by intake of these precursors, gut bacterial activity, and host conjugating enzyme activity. A single SDG dose results in enterolignan appearance in plasma 8-10 h later--a timeframe associated with colonic bacterial metabolism and absorption. Conjugation of enterolignans with sulfate and glucuronic acid occurs in the intestinal wall and liver, with the predominant conjugates being glucuronides. Controlled feeding studies have demonstrated dose-dependent urinary lignan excretion in response to flaxseed consumption (a source of SDG); however, even in the context of controlled studies, there is substantial interindividual variation in plasma concentrations and urinary excretion of enterolignans. The complex interaction between colonic environment and external and internal factors that modulate it likely contribute to this variation. Knowledge of this field, to date, indicates that understanding the sources of variation and measuring the relevant panel of compounds are important in order to use these measures effectively in evaluating the impact of lignans on human health.
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Enterolactone
Sesamin
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The mammalian lignans enterolactone and enterodiol, which are produced by the microflora in the colon of humans and animals from precursors in foods, have been suggested to have potential anticancer effects. This study determined the production of mammalian lignans from precursors in food bars containing 25 g unground whole flaxseed (FB), sesame seed (SB), or their combination (FSB; 12.5 g each). In a randomized crossover study, healthy postmenopausal women supplemented their diets with the bars for 4 wk each separated by 4-wk washout periods, and urinary mammalian lignan excretion was measured at baseline and after 4 wk as a marker of mammalian lignan production. Results showed an increase with all treatments (65.1-81.0 mumol/day; P < 0.0001), which did not differ among treatments. Lignan excretion with the whole flaxseed was similar to results of other studies using ground flaxseed. An unidentified lignan metabolite was detected after consumption of SB and FSB but not of FB. Thus, we demonstrated for the first time that 1) precursors from unground whole flaxseed and sesame seed are converted by the bacterial flora in the colon to mammalian lignans and 2) sesame seed, alone and in combination with flaxseed, produces mammalian lignans equivalent to those obtained from flaxseed alone.
Enterolactone
Crossover study
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Lignans in flaxseed have been part of the human diet for centuries. In 1955, the isolation and structure of the lignan derivative secoisolariciresinol diglucoside (SDG) was reported. The biological role of SDG and mammalian lignan metabolites enterodiol and enterolactone was initially reported 20 years later. Experimental evidences showed the beneficial effects of lignans on breast, colon, and thyroid cancer. A modified gas chromatography/mass spectrometry (GC/MS) assay was developed for lignans in serum and colon samples of rats fed flaxseed meal. The method developed for the analysis of metabolites involves extraction and derivatization of samples and quantitative analysis by selected ion monitoring using GC/MS. The levels of lignan metabolites enterodiol and enterolactone were determined to be 0.013 and 0.23 microM in serum samples and 0.008 and 1.63 microM in colon samples.
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Enterolactone
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Enterolactone
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Sesamin
Enterolactone
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The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented. Keywords: Phytoestrogens; lignans; matairesinol; secoisolariciresinol; lariciresinol; pinoresinol; syringaresinol; isolariciresinol; arctigenin; 7-hydroxymatairesinol; mammalian lignans; enterolactone; enterodiol
Enterolactone
Pinoresinol
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