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At least 361 records · Page 20Linked to original sources
PubMed2006

Urinary isoflavonoids as a dietary compliance measure among premenopausal women.

Clinical trials investigating the effects of soy food intake require high compliance with a dietary protocol. Measuring soy isoflavonoids in bodily fluids is the most objective method currently available in determining compliance to a soy diet. In the present study, we investigated how frequently the urinary isoflavonoid excretion rate (UIER) should be analyzed to provide a reasonably accurate measurement of dietary compliance without being a burden on the participants. Nineteen premenopausal women who were on a daily soy diet protocol collected first-morning urine samples over one menstrual cycle. Spearman rank order correlation coefficients (r) between the UIERs of total isoflavonoids for a single day, for a week, and for all weeks combined with the monthly UIER were high for all samples (single day: r = 0.89; Week 1: r = 0.89; Week 2:r = 0.85; Week 3: r = 0.75; all weeks combined UIER: r = 0.94) and remained high after stratification by ethnicity, body mass index, and equol-excretor status. According to these results, the analysis of UIERs from a single or weekly first-morning sample provides a highly accurate and more feasible method of determining dietary compliance among women with regular soy consumption than that from urine samples collected every morning during one month.

Adult↗
PubMedDate not supplied

An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection.

To study the safety and potential health benefits of soy isoflavones, a rapid and simple method based on liquid chromatography combined with mass spectrometry (LC/MS) and photodiode array detector (PDA) was developed for the determination of isoflavones in rat plasma. The analytes included daidzein, genistein, glycitein, equol, 4-ethyl phenol, and biochanin A over a concentration range of 1.0-4320.0 nM using 75 microL of rat plasma. Rat plasma samples were hydrolyzed by adding an enzyme mixture from Helix pomatia containing glucuronidase and sulfatase to convert the isoflavone beta-glycosides daidzin, genistin, and glycitin to their active aglycone forms. A liquid-liquid extraction method using ethyl acetate as the extraction solvent was used to extract aglycones and the internal standards (phenolphthalein beta-D glucuronide, 4-methylumbelliferyl sulfate, and apigenin) from digested plasma samples. The extract was evaporated to dryness under a nitrogen stream, reconstituted with 0.1% formic acid in water-acetonitrile (85 + 15), and injected into a Zorbax SB-CN reversed-phase column (4.6 x 75 mm, 3.5 microm particle size). The Micromass ZQ detector was operated in the positive ion selected-ion monitoring mode. The flow rate for LC was 1.0 mL/min, with a split where 25% of the effluent was introduced into the electrospray ionization probe of the MS instrument and 75% into the PDA. The chromatographic run time was 16.0 min, with delay of 10 min/injection. The interday precision and accuracy of the standard samples were <2.6% relative standard deviation and <10% relative error, respectively. Recovery of the reported isoflavones with this method varied from 86 to 100%.

Acetates↗
PubMedDate not supplied

Quantification of tamoxifen and metabolites and soy isoflavones in human plasma using liquid chromatography with electrospray ionization tandem mass spectrometry.

Tamoxifen is an important estrogen receptor antagonist used successfully for the treatment and prevention of breast cancer. The use of complementary and alternative medicines is an increasingly popular means for patients to participate in their own health care, and soy products, which contain phytoestrogens, have been widely promoted for possible beneficial effects on menopausal symptoms. The possibility that soy isoflavones could reduce tamoxifen efficacy has been demonstrated in animal models of post-menopausal breast cancer, but the occurrence of such an effect in women has not been explored. This paper describes the development and validation of a sensitive method using solid-phase extraction and isotope dilution liquid chromatography/tandem mass spectrometry with multiple reaction monitoring for the concurrent analysis of the major soy isoflavones (genistein and daidzein), an important metabolite of daidzein (equol), tamoxifen, and its important metabolites (4-hydroxytamoxifen, N-desmethyltamoxifen, and 4-hydroxy-N-desmethyltamoxifen or "endoxifen") in the serum of rats and women. The limits of quantification achieved are sufficient to determine accurately and precisely the concentrations of all of these analytes in women consuming soy foods and/or therapeutic doses of tamoxifen at levels consistent with modulation of estrogen receptor-mediated functions. These procedures enable future investigations of the possible impact of diet on the outcome of breast cancer therapy.

Animals↗
PubMed1995

Fecal lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder.

Lignans and isoflavonoids are diphenolic compounds found in plant foods, particularly whole grains and legumes. They have been shown to have anticarcinogenic properties in animal and cell studies, and have been associated with reduced cancer risk in epidemiological studies. In order to perform further epidemiological and metabolic studies on these compounds, it is necessary to be able to monitor concentrations in biological samples. In this study, we examined the effects of consumption of flaxseed, a concentrated source of lignans, on fecal lignan excretion and evaluated the effect of high lignan consumption on fecal excretion of isoflavonoids. Thirteen women were studied for two diet periods of three menstrual cycles each in a cross-over design. During the control period, they consumed their usual diets; during the treatment period they consumed their usual diets supplemented with 10 g/day ground flaxseed. Feces were collected on days 7-11 of the last menstrual cycle in each diet period. Five-day fecal composites were analyzed for lignans and isoflavonoids by isotope dilution gas chromatography-mass spectrometry. Fecal excretion of the lignans enterodiol, enterolactone, and matairesinol increased significantly with flax consumption, from 80.0 +/- 80.0 (SD) to 2560 +/- 3100; 640 +/- 480 to 10,300 +/- 7580; and 7.33 +/- 10.0 to 11.9 +/- 8.06 nmol/day, respectively. There were no differences in fecal excretion of the isoflavonoids, daidzein, equol, genistein, and O-demethylangolensin.

Adult↗
PubMed1994

Stimulation of pS2 expression by diet-derived compounds.

Epidemiological studies suggest a lowered risk of hormone-dependent cancers among vegetarians, but the basis for this association remains unclear. Vegetables and fruits contain certain compounds which can be converted to biologically active hormone-like substances, such as lignans and isoflavones, by intestinal flora. The interaction of these compounds with endogenous hormones may be a novel, diet-dependent mechanism in cancer prevention. To explore this possibility, we developed a rapid, specific assay system to screen for compounds with estrogen-like activity in tissue culture. We utilized the estrogen receptor-positive breast cancer cell MCF-7 and monitored the expression of the estrogen-responsive protein pS2 by Northern blots. Our results indicated that the phenolic compounds daidzein, equol, nordihydroguaiaretic acid, enterolactone, and kaempferol were able to elicit an estrogen-like response, while quercetin and enterodiol were not.

Breast Neoplasms↗
PubMed1996

Daidzein and genistein concentrations in human milk after soy consumption.

Soy isoflavones were quantified from human milk by a fast, precise, and selective HPLC method after enzymatic hydrolysis of conjugated isoflavones and extraction with ethyl acetate. Isoflavone aglycones and their mammalian metabolites equol and O-desmethylangolensin were separated selectively and identified by absorbance patterns, fluorometric and electrochemical detection, gas chromatography-mass spectrometric analysis after trimethylsilylation, and with internal and external authentic standards. HPLC injections of 20 microL of human milk showed detection limits of 1-3 pmol for all analytes by using diode-array detection. The detection limit could be improved by as much as 1000-fold by extended concentration through partitioning with ethyl acetate, by using electrochemical detection, by increasing the injection volumes, or by combining these techniques. We used the proposed method to monitor isoflavone concentrations in human milk and in human urine after challenge with 5, 10, and 20 g of roasted soybeans in the diet. Implications of the results for the potential of isoflavones to prevent cancer in newborn infants exposed to these agents are discussed.

Anticarcinogenic Agents↗
PubMed2004

Measurement of isoflavones using liquid chromatography with multi-channel coulometric electrochemical detection.

We evaluated the use of HPLC multi-channel coulometric electrochemical detection (HPLC-ECD) for the routine measurement of phytochemicals by analyzing standards and urine samples. Compounds were separated chromatographically and electrochemically with high sensitivity (10 ng/ml of isoflavones in urine). HPLC-ECD will enable better investigation into the relationship between lifestyle and the effects of phytochemicals on humans.

Chromatography, High Pressure Liquid↗
PubMed2000

Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids.

The polyphenolic structures of flavonoids and isoflavonoids confer them with the ability to scavenge free radicals and to chelate transition metals, a basis for their potent antioxidant abilities. Another possible contributory mechanism toward their antioxidant activities is their ability to stabilize membranes by decreasing membrane fluidity. In this study, the effects of representative flavonoids, isoflavonoids, and their metabolites on membrane fluidity and their preferential localization in the membrane were investigated using large unilamellar vesicles (LUVs) as the membrane models. These results were compared with those of cholesterol and alpha-tocopherol. Changes in fluorescence anisotropy values for a series of n-(9-anthroyloxy) fatty acid probes (n = 6, 12, 16) upon addition of the test compounds were used to monitor alterations in membrane fluidity at graded depths in lipid bilayer. The results of the study suggest that the flavonoids and isoflavonoids, similar to cholesterol and alpha-tocopherol, partition into the hydrophobic core of the membrane and cause a dramatic decrease in lipid fluidity in this region of the membrane. Localization of flavonoids and isoflavonoids into the membrane interiors and their resulting restrictions on fluidity of membrane components could sterically hinder diffusion of free radicals and thereby decrease the kinetics of free radical reactions.

Chromans↗
PubMed1984

Identification of the isoflavonic phytoestrogen daidzein in human urine.

The identification by gas chromatography-mass spectrometry of the isoflavonic phytoestrogen daidzein [7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one] for the first time in human urine is described. The metabolism and effect on reproduction of isoflavones in animals and the possible significance of phytoestrogens in man is discussed. Preliminary results on the quantitative excretion of daidzein in female subjects consuming different diets are also reported.

Chromans↗
PubMed1993

Plasma concentrations of phyto-oestrogens in Japanese men.

A low mortality from prostatic cancer is found in Japanese men consuming a low-fat diet with high content of soy products, a rich source of isoflavonoids. We therefore assayed four isoflavonoids in plasma of 14 Japanese and 14 Finnish men. The geometric mean plasma total individual isoflavonoid levels were 7 to 110 times higher in the Japanese than in the Finnish men. Genistein, a tyrosine kinase inhibitor, occurred in the highest concentration (geometric mean 276 nmol/L). We hypothesise that these high phyto-oestrogen levels may inhibit the growth of prostatic cancer in Japanese men, which may explain the low mortality from prostatic cancer in that country.

Chromans↗
PubMed1985

Oestrogenic potency of genistin and daidzin in mice.

The oestrogenic activity of genistin and daidzin was investigated in the B6D2F1 strain of mouse. Diethylstilboestrol and genistein were used as positive controls. The oestrogenic response to 1.5 mg genistin was equivalent to that of 1 mg genistein, giving a 1:1 molar relationship in oestrogenic activity between genistin and genistein. The oestrogenic response to 3.8 mg daidzin was equivalent to that of 1 mg genistein. Analysis of the blood obtained from the mice in this experiment failed to reveal any free genistein or daidzein in the plasma.

Animals↗
PubMed2003

Oestrogenic compounds and oxidative stress (in human sperm and lymphocytes in the Comet assay).

Reactive oxygen species (ROS) are produced by a wide variety of chemicals and physiological processes in which enzymes catalyse the transfer of electrons from a substrate to molecular oxygen. The immediate products of such reactions, superoxide anion radicals and hydrogen peroxide can be metabolised by enzymes such as superoxide dismutase (SOD) and catalase (CAT), respectively, and depending on its concentration by Vitamin C (Vit C). Under certain circumstances the ROS form highly reactive hydroxyl radicals. We examined human sperm and lymphocytes after treatment with six oestrogenic compounds in the Comet assay, which measures DNA damage, and observed that all caused damage in both cell types. The damage was diminished in nearly all cases by catalase, and in some instances by SOD and Vit C. This response pattern was also seen with hydrogen peroxide. This similarity suggests that the oestrogen-mediated effects could be acting via the production of hydrogen peroxide since catalase always markedly reduced the response. The variable responses with SOD indicate a lesser involvement of superoxide anion radicals due to SOD-mediated conversion of superoxide to hydrogen peroxide generally causing a lower level of DNA damage than other ROS. The variable Vit C responses are explained by a reduction of hydrogen peroxide at low Vit C concentrations and a pro-oxidant activity at higher concentrations. Together these data provide evidence that inappropriate exposure to oestrogenic compounds could lead to free-radical mediated damage. It is believed that the observed activities were not generated by cell free cell culture conditions because increased responses were observed over and above control values when the compounds were added, and also increasing dose-response relationships have been found after treatment with such oestrogenic compounds in previously reported studies.

Adult↗
PubMed2001

Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones.

It is generally not known that most commercial rodent diets are formulated with soy protein and deliver large daily doses of isoflavones to animals throughout their lifespan, including the in utero period. Here, we demonstrate that isoflavones are bioavailable and show that commercial rodent diets universally used by animal facilities lead to very high steady-state serum isoflavone concentrations in adult rats (2613 +/- 873 ng/mL) and mice (2338 +/- 531 ng/mL), exceeding the animal's endogenous estrogen level by 30,000- to 60,000-fold. We demonstrate the maternal-fetal intrauterine transfer of isoflavones in animals fed a standard Purina 5001 soy-containing diet and show that newborn rat pups have high serum isoflavones levels (540 +/- 174 ng/mL) that are maintained throughout the suckling period by passage of isoflavones into maternal milk. These findings have profound implications for all animal experiments, including multigenerational studies and studies of transgenic animals, especially if biochemical or morphological end-points are influenced by the hormonal or nonhormonal properties of phytoestrogens. These compounds have the potential to modulate genotypic and phenotypic expression in general, and therefore, all investigators should be vigilant to the phytoestrogen composition of commercial rodent diets because there is a history of potent biological effects in larger animals and in humans from high circulating isoflavone concentrations.

Age Factors↗
PubMed2006

Validation and application of a robust yeast estrogen bioassay for the screening of estrogenic activity in animal feed.

Previously we described the construction and properties of a rapid yeast bioassay stably expressing human estrogen receptor alpha (hERalpha) and yeast enhanced green fluorescent protein (yEGFP), the latter in response to estrogens. In the present study this yeast estrogen assay was validated as a qualitative screening method for the determination of estrogenic activity in animal feed. This validation was performed according to EC Decision 2002/657. Twenty blank animal feed samples, including milk replacers and wet and dry feed samples, were spiked with 17beta-estradiol (E2beta) at 5 ng g(-1), 17alpha-ethynylestradiol (EE2) at 5 ng g(-1), diethylstilbestrol (DES) at 10 ng g(-1), zearalenone at 1.25 microg g(-1) or equal at 200 microg g(-1). All of these blank and low estrogen spiked feed samples fulfilled the CCalpha and CCbeta criterions, meaning that all 20 blank feed samples gave a signal below the determined decision limit CCalpha and were thus classified as compliant, and at least 19 out of the 20 spiked samples gave a signal above this CCalpha (beta = 5%) and were thus classified as suspect. The method was specific and estrogens in feed were stable for up to 98 days. In this study we also present long-term performance data and several examples of estrogens found in the routine screening of animal feed. This is the first successful example of a developed, validated and applied bioassay for the screening of hormonal substances in feed.

Animal Feed↗
PubMed2005

Effect of pure genistein on bone markers and hot flushes.

OBJECTIVE: To evaluate the effect of 90 mg of daily genistein on markers of bone turnover and menopausal symptoms. DESIGN: This was a cross-over, placebo-controlled study involving 100 postmenopausal women. Subjects were randomly assigned to daily genistein or placebo for 6 weeks and crossed over to the alternative preparation for the following 6 weeks. Pure genistein was processed and encapsulated in accordance with British Pharmacopoeia standards. Each capsule contained 90 mg of pure genistein while the placebo contained just the recipients. RESULTS: In women with significant hot flushes (score (intensity x number) > or = 9), genistein reduced symptoms by 30% compared to baseline and the difference compared to placebo was statistically significant. No effect was observed on biochemical markers of bone turnover, possibly due to the short duration of each arm of the study. Genistein reduced osteocalcin, a marker of bone formation, by 3.6% compared to baseline and 0.31% compared to placebo (p = 0.81 and 0.40, respectively). Genistein increased cross-link telopeptide, a marker of bone resorption, by 1.8% compared to baseline and 0.29% compared to placebo; both differences were not statistically significant (p = 0.078 and 0.88, respectively). CONCLUSION: Pure genistein at a dose of 90 mg per day appears to reduce the number of hot flushes in postmenopausal women but the effect is mild.

Biomarkers↗
PubMed1998

Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans.

The aim of this study was to determine the pharmacokinetics and urinary excretion patterns of the soy isoflavones daidzein and genistein in humans. Six healthy men with a mean age of 37 y and a mean body mass index (in kg/m2) of 24 consumed a soybean flour-based meal on two occasions approximately 6 d apart. Blood samples and total urine were collected at intervals for the measurement of daidzein and genistein with HPLC. Isoflavone concentrations rose slowly and reached maximum values of 3.14 +/- 0.36 micromol/L at 7.42 +/- 0.74 h for daidzein and 4.09 +/- 0.94 micromol/L at 8.42 +/- 0.69 h for genistein. Elimination half-lives were 4.7 +/- 1.1 and 5.7 +/- 1.3 h for daidzein and genistein, respectively. The slow increase in plasma concentrations is consistent with the facilitation of absorption by hydrolysis in the small and large intestines of the glycosidic forms of the isoflavones present in soybean-containing foods to their corresponding aglycones. The rate of urinary excretion of daidzein was greater than that of genistein throughout the postmeal period, with mean recoveries of 62 +/- 6% and 22 +/- 4% (P < 0.001) for daidzein and genistein, respectively. However, the ratio of the areas under the plasma concentration versus time curves for genistein and daidzein was equal to the ratio of the concentrations of the respective isoflavones in the soy meal. It is concluded that the bioavailabilities of daidzein and genistein are similar, not withstanding the difference in urinary excretion.

Adult↗
PubMed2003

Comparing the pharmacokinetics of daidzein and genistein with the use of 13C-labeled tracers in premenopausal women.

BACKGROUND: Despite significant interest in the risks and benefits of phytoestrogens to human health, few data exist on their pharmacokinetics in humans. OBJECTIVE: We investigated the pharmacokinetics of the (13)C isotopic forms of daidzein and genistein in healthy humans, specifically addressing intraindividual variability, effect of increasing intake, and influence of prolonged exposure to a soy food diet. DESIGN: Premenopausal women (n = 16) were administered 0.4 mg [(13)C]daidzein or [(13)C]genistein/kg body wt orally on 3 occasions, including once after eating soy foods for 7 d. On a further occasion the dose was doubled. Plasma and urinary [(13)C]isoflavone concentrations were measured by mass spectrometry. RESULTS: Serum concentrations of [(13)C]genistein and [(13)C]daidzein peaked after 5.5 and 7.4 h, respectively. The systemic bioavailability and maximum serum concentration of [(13)C]genistein were significantly greater than those of [(13)C]daidzein. The bioavailability of both isoflavones did not increase linearly when the dietary intake was doubled. The mean volume of distribution normalized to bioavailability (V(d)/F), clearance rate, and half-life of [(13)C]daidzein were 336.25 L, 30.09 L/h, and 7.75 h, respectively; the corresponding values for [(13)C]genistein were 258.76 L, 21.85 L/h, and 7.77 h. The average recovery of [(13)C]daidzein and [(13)C]genistein in urine was 30.1% and 9.0% of the dose ingested, respectively. CONCLUSIONS: The serum pharmacokinetics of [(13)C]daidzein and [(13)C]genistein were reproducible among healthy women, and genistein was more bioavailable than was daidzein. Pharmacokinetics were unaffected by chronic exposure to soy foods. Urinary isoflavone concentrations correlated poorly with maximal serum concentrations, indicating the limitations of urine measurements as a predictor of systemic bioavailability. The bioavailability of both isoflavones was nonlinear at higher intakes, suggesting that uptake is rate-limiting and saturable.

Adult↗