Excretion, isolation and structure of a new phenolic constituent of female urine

Stitch, S. R.; Toumba, Jack; Groen, Marinus B.; Funke, Carel W.; Leemhuis, J.; Vink, Jan; Woods, G. Forrest

doi:10.1038/287738a0

Cited by 164 publications

(58 citation statements)

References 3 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%

“…When assessing sex differences, detailed information on the menstrual cycle should be given too. Early studies showed that enterolignan excretion is associated with pregnancy and the menstrual cycle, although the number of samples analysed was limited (Setchell et al 1979;Stitch et al 1980). The possible role of progesterone detailed above would partly explain higher excretion of enterolignans during the mid-luteal phase and early pregnancy.…”

Section: Blood Levels In Relation To Bacterial Conversion Of Lignansmentioning

confidence: 99%

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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%

Section: Blood Levels In Relation To Bacterial Conversion Of Lignansmentioning

confidence: 99%

Bioavailability of lignans in human subjects

2006

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“…When consumed, the plant isoflavonoids and lignans undergo many metabolic conversions in the gut, which results in the formation of hormonelike compounds with estrogen activity and the ability to bind weakly to estrogen receptors (16 (17,18). Furthermore, small amounts of four plant lignans (matairesinol, lariciresinol, isolariciresinol, and secoisolariciresinol) have been identified in human urine (19,20); 7'-hydroxymatairesinol and 7'-hydroxyenterolactone were also tentatively identified in urine (21).…”

Section: Phytoestrogens Identified In Manmentioning

confidence: 99%

Phytoestrogens: Epidemiology and a Possible Role in Cancer Protection

Adlercreutz¹

1995

Environmental Health Perspectives

130

110

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Because many diseases of the Western Hemisphere are hormone-dependent cancers, we have postulated that the Western diet, compared to a vegetarian or semivegetarian diet, may alter hormone production, metabolism, or action at the cellular level by some biochemical mechanisms. Recently, our interest has been mainly focused on the cancer-protective role of some hormonelike diphenolic phytoestrogens of dietary origin, the lignans and the isoflavonoids. The precursors of the biologically active compounds originate in soybean products (mainly isoflavonoids), whole grain cereal food, seeds, and probably berries and nuts (mainly lignans). The plant lignan and isoflavonoid glycosides are converted by intestinal bacteria to hormonelike compounds with weak estrogenic but also antioxidative activity; they have now been shown to influence not only sex hormone metabolism and biological activity but also intracellular enzymes, protein synthesis, growth factor action, malignant cell proliferation, differentiation, and angiogenesis in a way that makes them strong candidates for a role as natural cancer-protective compounds. Epidemiologic investigations strongly support this hypothesis because the highest levels of these compounds in the diet are found in countries or regions with low cancer incidence. This report is a review on recent results suggesting that the diphenolic isoflavonoids and lignans are natural cancer-protective compounds. -Environ Health Perspect 103(Suppl 7):103-1 12 (1995)

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“…Recently, a novel compound, enterolactone (HPMF), has been isolated from human urine (65,66) (Fig. 8).…”

Section: Phytoestrogensmentioning

confidence: 99%

Structure-Activity Relationships of Estrogens

Jordan¹,

Mittal²,

Gosden³

et al. 1985

Environmental Health Perspectives

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The last 50 years has seen an exponential rise in the published reports about estrogen action. The model to describe the early events in the mechanism of action of estrogens via the estrogen receptor is updated in this paper to incorporate some of the recent data on the subcellular localization of the receptor. New evidence suggests that the receptor is a nuclear protein, so it appears that estrogens must first diffuse into the nuclear compartment to initiate estrogen action via the receptor complex. This review traces the development of potent estrogenic compounds by the study of their structure-activity relationships. Studies of structure-activity relationships in vivo using Allen Doisy or 3-day uterine weight tests can provide much valuable information, but the assays suffer from the complex problems of pharmacokinetics and metabolic transformation. Studies in vitro using primary cultures of rat pituitary or uterine cells to assay the ability of a compound to induce prolactin synthesis or progesterone receptor synthesis, respectively, can provide essential information about the structural requirements for a compound to produce estrogenic effects. Nevertheless, it should be pointed out that studies in vivo are required to determine whether a compound is metabolically activated to an estrogen. Estrogen receptor binding models are presented to describe the changes in a molecule that will predict high affinity for the ligand and agonist, partial agonist and antagonist properties of the ligand-receptor complex. Most estrogenic pesticides and phytoestrogens comform to the predictions of the estrogen receptor binding model.

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Excretion, isolation and structure of a new phenolic constituent of female urine

Cited by 164 publications

References 3 publications

Bioavailability of lignans in human subjects

Bioavailability of lignans in human subjects

Phytoestrogens: Epidemiology and a Possible Role in Cancer Protection

Structure-Activity Relationships of Estrogens

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