The definitive identification of the lignans trans-2,3-bis(3-hydroxybenzyl)-γ-butyrolactone and 2,3-bis(3-hydroxybenzyl)butane-1,4-diol in human and animal urine

Setchell, Kenneth D.R.; Lawson, A. M.; Conway, EM; Taylor, Norman; Kirk, D. N.; Cooley, G.; Farrant, R. D.; WYNN, S.; Axelson, Magnus

doi:10.1042/bj1970447

Cited by 93 publications

(28 citation statements)

References 22 publications

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“…(2005b), the total amount of ED and EL detected in urine was 40 % of the ingested dose of 500 mg SDG, the majority of which was excreted within 2 d. The residence time of enterolignans was lower in women than in men (17·3 v. 23·9 h). In earlier studies (Stitch et al 1980;Setchell et al 1981), both enantiomers of EL were detected in urine and the authors proposed that urinary EL is racaemic.…”

Section: Urinary Excretionmentioning

confidence: 99%

Bioavailability of lignans in human subjects

2006

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Dietary lignans are phyto-oestrogens that possibly influence human health. The present review deals with lignan bioavailability, the study of which is crucial to determine to what extent metabolism, absorption and excretion of lignans alter their biological properties. Since intestinal bacteria play a major role in lignan conversion, for instance by producing the enterolignans enterodiol and enterolactone, emphasis is put on data obtained in recent bacteriological studies.

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Section: Urinary Excretionmentioning

confidence: 99%

Bioavailability of lignans in human subjects

2006

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“…On the other hand, these and other in vivo studies [26,49] show that lignans do not induce classical estrogenic or antiestrogenic effects in female or male rodent reproductive organs (e. g., uterine growth in immature females, or regression of male accessory sex glands). However, dietary flaxseed or SDG supplementation of adult virgin or pregnant rats induced changes in estrous cycle and resulted in persistent estrogen-like effects in the offspring [50,51].…”

Section: Lignans In Breast Cancer Preventionputative Mechanisms and Tmentioning

confidence: 94%

Role of dietary lignans in the reduction of breast cancer risk

Saarinen¹,

Wärri

Airio

et al. 2007

Molecular Nutrition Food Res

116

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Lignans are a large group of fiber-associated phenolic compounds widely distributed in edible plants. Some of the ingested plant lignans are converted by intestinal microbiota to enterolignans, enterodiol (END) and enterolactone (ENL), the latter of which has been thought to be the major biologically active lignan, and suggested to be associated with low risk of breast cancer. In line with this, administration of plant lignans which are further metabolized to ENL, or ENL as such, have been shown to inhibit or delay the growth of experimental mammary cancer. The mechanism of anticarcinogenic action of ENL is not yet fully understood, but there is intriguing evidence for ENL as a modulator of estrogen signaling. These findings have generated interest in the use of lignans as components of breast cancer risk reducing functional foods. Identification of target groups, who would benefit most, is of pivotal importance. Therefore, further identification and validation of relevant biomarkers, which can be used as indicators of lignan or ENL action and breast cancer risk reduction at different stages of the disease, are of importance.

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“…Lignans are widely distributed as minor constituents of some plant species (Haworth & Slinger, 1940), and are defined as compounds possessing a 2,3-dibenzylbutane structure (Rao, 1978). The mammalian lignans, enterodiol and enterolactone, differ significantly in chemical structure from plant lignans in that they have a phenolic hydroxyl group substituted on the meta position of the aromatic ring (Setchell et al 1981).…”

Section: S T R U C T U R E a N D S O U R C E Smentioning

confidence: 99%

“…The isoflavone metabolite, equol, is thought to be derived from isoflavone precursors. Absorbed phyto-oestrogens are transported to the liver via the hepatic portal vein, where they are rapidly conjugated with glucuronic acid, and to a much lesser extent with sulphuric acid, by the liver (Axelson & Setchell, 1980;Setchell et al 1981Setchell et al , 1984; Fig. 2).…”

Section: E C H a N I S M S Of A C T I O N A N D M E T A B O L I S Mmentioning

confidence: 99%

Physiological effects of phyto-oestrogens in relation to cancer and other human health risks

Cassidy

1996

Proc. Nutr. Soc.

123

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Effets physiologiques des phytoestroghes en relation avec le cancer et autres risques sur la santC de l'homme RESUME Les aliments d'origine vCgCtale contiennent des phytoestrogknes dont la structure est semblable h l'oestrogkne des mammifkres, l'estradiol-17P. 11s ont une affinitC pour les rCcepteurs de I'oestrogkne entre 1/500 et 1/1000 comparCe a celle de 170estrog&ne-17P, et ils produisent des rCponses oestrogeniques typiques et prkvisibles lorsqu'ils sont administrCs aux animaux. Dans les modkles animaux et dans les systbmes expkrimentaux in vitro, les phytoestrogknes se montrent capables d'agir la fois comme agonistes partiels et comme antagonistes partiels, avec des effets primaires favorisCs par la competition avec l'estradiol-17P pour le rkcepteur de l'oestrogbne. Les isoflavones, administrCs comme produits de protCine de soja, ont modifiC le statut hormonal et la regulation physiologique du cycle menstruel chez des femmes avant la mCnopause. Aucun de ces changements n'a CtC observe lorsque le soja a Ct C remplacd par de 1'Arcon F, un produit de soja sans isoflavone. Ces rCsultats suggbrent donc que les oestrogknes vCgCtaux presents dans le soja exercent potentiellement un effet oestrogCnique faible sur l'axe hypothalamique-pituitaire-gonadique. I1 est possible que 1'Ctat de conjugaison des isoflavones de l'alimentation influence les effets physiologiques observCs, les isoflavones inconjuguCs Ctant potentiellement plus efficaces. Dans des essais en appartement mCtabolique sur des femmes mCnopausCes, on a observC que 60 g/jour de soja sur une pCriode de quatre semaine supprimaient les niveaux de luteinizing hormone (LH), alors que 40 g/jour de graine de lin (une riche source de lignanes) sur une pCriode de six semaines causaient une suppression significative de LH aussi bien que de follicle-stimulating hormone.I1 est possible que les modifications hormonales et du cycle menstruel induites par la protCine de soja et la graine de lin sur les femmes avant et aprbs la mknopause soient potentiellement bCnCfiques au regard des facteurs de risque du cancer du sein. Des preuves CpidCmiologiques, des rCsultats d'Ctudes sur des animaux, et certains travaux in vitro suggbrent Cgalement que les phytoestrogknes pourraient avoir un r61e protecteur dans le dCveloppement du cancer du sein. Les donnCes exPCrimentales des Ctudes sur le r61e protecteur exercC par les phytoestrogbnes dans la prkvention du cancer de la prostate sont moins convaincantes.I1 est Cvident que ces composCs sont absorb&, mais il y a une grande variabilitt individuelle dans leur mCtabolisme. Des travaux plus approfondis devraient chercher a Ctudier le mCtabolisme des phytoestrogknes in vivo pour expliquer la grande variabilitd individuelle dans I'excrCtion de ces composks.

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The definitive identification of the lignans trans-2,3-bis(3-hydroxybenzyl)-γ-butyrolactone and 2,3-bis(3-hydroxybenzyl)butane-1,4-diol in human and animal urine

Cited by 93 publications

References 22 publications

Bioavailability of lignans in human subjects

Bioavailability of lignans in human subjects

Role of dietary lignans in the reduction of breast cancer risk

Physiological effects of phyto-oestrogens in relation to cancer and other human health risks

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