Lignan and isoflavonoid conjugates in human urine

Adlercreutz, Herman; Wildt, Jolande van der; Kinzel, Judith; Attalla, Hesham; Wähälä, Kristiina; Mäkelä, Taru; Hase, Tapio; Fotsis, Theodore

doi:10.1016/0960-0760(94)00146-d

Cited by 200 publications

(118 citation statements)

References 28 publications

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“…Phytoestrogens have been measured in urine (Adlercreutz et al, 1986(Adlercreutz et al, , 1991(Adlercreutz et al, , 1995bHorn-Ross et al, 1997;Roach et al, 1998, Lampe et al, 1998Uehar et al, 2000;Dai et al, 2002;Kim et al, 2002;Valentı´n-Blasini et al, 2003); feces (Adlercreutz et al, 1995a); serum (Anderson et al, 1995;Stumpf et al, 2000;Morton et al, 2002 Figure 1. A schematic representation of the reported metabolism of isoflavones (a) and lignans (b).…”

Section: Introductionmentioning

confidence: 99%

Urinary phytoestrogen concentrations in the U.S. population (1999–2000)

Valentín-Blasini

Sadowski

Walden

et al. 2005

J Expo Sci Environ Epidemiol

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We report population-based urinary concentrations of phytoestrogens stratified by age, sex, and composite racial/ethnic variables. We measured the isoflavones F genistein, daidzein, equol, and O-desmethylangolensin (O-DMA) F and the lignans F enterolactone and enterodiol F in approximately 2500 urine samples from individuals aged 6 years and older who participated in the National Health and Nutrition Examination Survey (NHANES) in 1999 and 2000. We detected all phytoestrogens in over 70% of the samples analyzed; enterolactone was detected in the highest concentrations, and daidzein was detected with the highest frequency. The geometric means for each phytoestrogen were as follows: genistein, 22.3 mg/g; daidzein, 68.6 mg/g; equol, 7.65 mg/g; O-DMA, 3.95 mg/g; enterolactone, 217 mg/g; and enterodiol, 24.3 mg/g creatinine. The 95th percentiles for each phytoestrogen were as follows: genistein, 380 mg/g; daidzein, 944 mg/g; equol, 50.3 mg/g; O-DMA, 217 mg/g; enterolactone, 2240 mg/g; and enterodiol, 240 mg/g creatinine. Multivariate analyses showed statistically significant differences among many of the demographic subgroups. Adolescents had higher concentrations of genistein and equol than adults. Non-Hispanic whites had higher concentrations of enterodiol and equol than Mexican Americans or non-Hispanic blacks. Non-Hispanic whites also had higher concentrations of enterolactone and O-DMA than Mexican Americans. Mexican Americans had higher concentrations of genistein than non-Hispanic blacks; however, the opposite was found for O-DMA. Determination of phytoestrogen exposure in the US population will help us to better understand phytoestrogen consumption in the US and will assist us in elucidating the potential role of phytoestrogens in protecting against cancer and heart disease.

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Section: Introductionmentioning

confidence: 99%

Urinary phytoestrogen concentrations in the U.S. population (1999–2000)

Valentín-Blasini

Sadowski

Walden

et al. 2005

J Expo Sci Environ Epidemiol

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“…Isoflavones are metabolized and then excreted as glucuronide, sulfate, and sulfoglucuronide conjugates in human urine (Doerge et al, 2000;Shelnutt et al, 2002). The conjugated compounds are generally converted to free aglycones by selective enzymatic hydrolysis and then analyzed by HPLC (Morand et al, 2001) or LC-MS methods (Maskarinec et al, 2007) that require less sample preparation than gas chromatography or gas chromatography-MS methods (Adlercreutz et al, 1995;Heinonen et al, 2003). These methods, however, provide data only on total glucuronides, sulfates, and free aglycones.…”

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confidence: 99%

Plasma Profiling of Intact Isoflavone Metabolites by High-Performance Liquid Chromatography and Mass Spectrometric Identification of Flavone Glycosides Daidzin and Genistin in Human Plasma after Administration of Kinako

Hosoda¹,

Furuta²,

Yokokawa³

et al. 2008

Drug Metab Dispos

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ABSTRACT:The roles of isoflavones in the prevention of several hormonedependent cancers and osteoporosis are of great interest. Despite many pharmacokinetics studies of the isoflavones, the actual types of conjugates circulating in the body and the position(s) of conjugation sites on the flavone skeleton are still uncertain because, in general, conjugated compounds in biological fluids have been evaluated by measuring the free aglycones obtained after selective enzymatic hydrolysis. Using an high-performance (HPLC)-UV-diode-array detector (DAD) method combined with solid-phase extraction, we have obtained HPLC profiles of isoflavone glycosides [daidzin (Din) and genistin (Gin)] and of intact isoflavone metabolites in human plasma: daidzein, genistein, daizein-7-glucuronide, daidzein-4-glucuronide, genistein-7-glucuronide, genistein-4-glucuronide, daidzein-7-sulfate, daidzein-4-sulfate, genistein-7-sulfate, and genistein-4-sulfate. We investigated the plasma profile of intact isoflavone metabolites in plasma obtained 1 to-7 h after orally administration of 50 g of kinako (baked soybean powder) to two healthy volunteers. The results of DAD analysis indicated that the main isoflavone metabolite peaks were identified on the HPLC chromatogram. Furthermore, the intact glycosides Din and Gin were detected in 1-h plasma samples by their positive electrospray ionization mass spectra, demonstrating that the glycosides Din and Gin can be absorbed from the gut.

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“…In our preliminary trial, no spot including equol was detected in the normal phase TLC system without ␤ -glucuronidase treatment. Adlercreutz et al reported that more than 60% of urinary isoflavonoids occurred as the monoglucuronide, and daidzein and equol, in particular, were excreted to a relatively high extent as sulfoglucuronides ( 20 ).…”

Section: Resultsmentioning

confidence: 99%

Rapid and Convenient Detection of Urinary Equol by Thin-Layer Chromatography

Yokoyama

Kuzuguchi

2007

J Nutr Sci Vitaminol

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Summary Equol, a metabolite of daidzein for some intestinal microflora, is known to retain highly estrogenic activity and is of wide interest in relation to human health. However, not all humans can produce equol. In this study, detection of urinary equol using thinlayer chromatography (TLC) was performed to distinguish between equol producers and non-producers. After 36 h of soy food intake, urine, collected from 7 volunteers, was hydrolyzed, purified by reverse phase silica gel column and applied to normal phase TLC. Consequently, equol was clearly separated from the urine samples and discriminated the equol producers in this system. The detection limit of equol was at least 20 ng.

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Lignan and isoflavonoid conjugates in human urine

Cited by 200 publications

References 28 publications

Urinary phytoestrogen concentrations in the U.S. population (1999–2000)

Urinary phytoestrogen concentrations in the U.S. population (1999–2000)

Plasma Profiling of Intact Isoflavone Metabolites by High-Performance Liquid Chromatography and Mass Spectrometric Identification of Flavone Glycosides Daidzin and Genistin in Human Plasma after Administration of Kinako

Rapid and Convenient Detection of Urinary Equol by Thin-Layer Chromatography

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