Human metabolism of mammalian lignan precursors in raw and processed flaxseed

Nesbitt, Paula D.; Lam, Yi; Thompson, Lilian U.

doi:10.1093/ajcn/69.3.549

Cited by 176 publications

(118 citation statements)

References 28 publications

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“…In human intestinal tract, SDG is converted by bacteria to mammalian lignans: enterodiol (ED) and enterolactone (EL) [3]. Due to the similarity in the chemical structure of ED and EL with oestradiol, both compounds can act as weak estrogenic/antiestrogenic compounds [4].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Activity of Flaxseed Extracts in Lipid Systems

et al. 2015

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Abstract:The aim of this work was to compare the antioxidant activity of the extract of flaxseed and its alkaline hydrolysate in two model systems: lipid autoxidation of triacylglycerols of sunflower oil (TGSO)-in a homogeneous lipid media and during β-carotene-linoleate emulsion system. In addition, pure lignans were tested. The material was defatted with hexane and then phenolic compounds were extracted using dioxane-ethanol (50:50, v/v) mixture. Carbohydrates were removed from the crude extract using an Amberlite XAD-16 column chromatography. The content of total phenolic compounds in the crude extract and after alkaline hydrolysis was determined using a Folin-Ciocalteu's phenol reagent. Individual phenolic compounds were determined by nordihydroguaiaretic acid (RP-HPLC) method in gradient system. The alkaline hydrolysis increased the content of total phenolics in the extract approximately by 10%. In the extracts of flaxseed, phenolic compounds were present in the form of macromolecular complex. In the alkaline hydrolysate, secoisolariciresinol diglucoside (SDG) was found as the main phenolic compound. Small amounts of p-coumaric and ferulic acids were also determined. SDG and both extracts were not able to inhibit effectively lipid autoxidation. The kinetics of TGSO autoxidation at 80˝C in absence and in presence of the extract before hydrolysis (EBH) and after hydrolysis (EAH) was monitored and compared with known standard antioxidants. Ferulic acid (FA) and butylated hydroxyl toluene (BHT) showed much higher antioxidant efficiency and reactivity than that of both extracts. Secoisolariciresinol (SECO) showed a higher activity in both model systems than SDG. However, the activity of SECO was much lower than that of nordihydroquaiaretic acid (NDGA).

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Section: Introductionmentioning

confidence: 99%

Antioxidant Activity of Flaxseed Extracts in Lipid Systems

et al. 2015

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“…The chemical structures of SDG and its mammalian metabolite enterolactone 39 are shown in Figure 1. Enterolactone and enterodiol are anaerobically formed via colonic 40 bacterial fermentation [6][7]. Besides the bacterial fermentation, enterolactone and enterodiol can 41 also be formed by other cell organelles such as a study that showed liver microsomes could 42 generate lignan aglycones [8].…”

Section: Introduction 36mentioning

confidence: 99%

Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside

Ayella¹,

Lim²,

Jiang³

et al. 2010

Nutrition Research

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“…Microflora in the colon (Setchell et al, 1981) convert plant lignans into enterolignans, which are detectable in blood and urine. Their levels have been correlated with the amount of plant lignans ingested (Nesbitt et al, 1999).In a recent meta-analysis, an inverse dose-response relationship was shown between breast cancer risk and soy-food intake in Asian, but not in Western women (Wu et al, 2008). Lignans have been shown to exhibit anti-carcinogenic properties (Wang et al, 1994;Prasad 2000;Bergman Jungeström et al, 2007), and it is hypothesised that exposure to high levels may be associated with a reduction in breast cancer risk.…”

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Lignans and breast cancer risk in pre- and post-menopausal women: meta-analyses of observational studies

et al. 2009

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Phyto-oestrogens are plant compounds structurally similar to oestradiol, which have been proposed to have protective effects against breast cancer. The main class of phyto-oestrogens in the Western diet is lignans. Literature reports on the effect of lignans in breast cancer risk have been conflicting. We performed three separate meta-analyses to examine the relationships between (i) plant lignan intake, (ii) enterolignan exposure and (iii) blood enterolactone levels and breast cancer risk. Medline, BIOSIS and EMBASE databases were searched for publications up to 30 September 2008, and 23 studies were included in the random effects meta-analyses. Overall, there was little association between high plant lignan intake and breast cancer risk (11 studies, combined odds ratio (OR): 0.93, 95% confidence interval (95% CI): 0.83 -1.03, P ¼ 0.15), but this association was subjected to marked heterogeneity (I 2 ¼ 44%). Restricting the analysis to post-menopausal women, high levels of plant lignan intake were associated with reduced breast cancer risk (7 studies, combined OR: 0.85, 95% CI: 0.78, 0.93, Po0.001) and heterogeneity was markedly reduced (I 2 ¼ 0%). High enterolignan exposure was also associated with breast cancer (5 studies, combined OR: 0.73, 95% CI: 0.57, 0.92, P ¼ 0.009) but, again, there was marked heterogeneity (I 2 ¼ 63%). No association was found with blood enterolactone levels (combined OR: 0.82, 95% CI: 0.59 -1.14, P ¼ 0.24). In conclusion, plant lignans may be associated with a small reduction in post-menopausal breast cancer risk, but further studies are required to confirm these results. (Beral, 2003) have both been associated with increased breast cancer risk. Isoflavones and lignans are plant compounds structurally similar to 17b-oestrodiol known as phyto-oestrogens, capable of oestrogen receptor binding (Kuiper et al, 1998;Mueller et al, 2004). Isoflavones are mostly found in soybean products, which are a staple of the Asian diet, whereas lignans are the principal group of phyto-oestrogens in Western diets. Lignans are more widespread in foods than isoflavones and are present in grain cereals, vegetables, seeds, tea and coffee (Mazur, 1998a;Mazur et al, 1998b). Microflora in the colon (Setchell et al, 1981) convert plant lignans into enterolignans, which are detectable in blood and urine. Their levels have been correlated with the amount of plant lignans ingested (Nesbitt et al, 1999).In a recent meta-analysis, an inverse dose-response relationship was shown between breast cancer risk and soy-food intake in Asian, but not in Western women (Wu et al, 2008). Lignans have been shown to exhibit anti-carcinogenic properties (Wang et al, 1994;Prasad 2000;Bergman Jungeström et al, 2007), and it is hypothesised that exposure to high levels may be associated with a reduction in breast cancer risk. However, results from a number of studies in Western populations have been variable. The aim of our systematic review was to establish whether an association exists between lignan exposure and breast cancer ris...

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Human metabolism of mammalian lignan precursors in raw and processed flaxseed

Abstract: Mammalian lignan production from flaxseed precursors is dependent on time and dose but not on processing.

Cited by 176 publications

References 28 publications

Antioxidant Activity of Flaxseed Extracts in Lipid Systems

Antioxidant Activity of Flaxseed Extracts in Lipid Systems

Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside

Lignans and breast cancer risk in pre- and post-menopausal women: meta-analyses of observational studies

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