Glucuronidation of the environmental oestrogen bisphenol A by an isoform of UDP-glucuronosyltransferase, UGT2B1, in the rat liver

Yokota, Hiroshi; Iwano, Hidetomo; Endo, M; Kobayashi, Tsutomu; Inoue, Hiroki; Ikushiro, Shinichi; Yuasa, Akira

doi:10.1042/bj3400405

Cited by 153 publications

(88 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Hence, variation in BPA-metabolic enzymes may bring out alteration in BPA inactivation/disposal paradigms. Among phase II enzymes, sulfotransferases (SULTs) and uridine diphosphate glucuronosyltransferases (UGTs) are known to be involved in BPA metabolism (Elsby et al 2001;Yokota et al 1999;Suiko et al 2000;Raftogianis et al 1997). Among SULTs, SULT1A1 is thought to sulfate phenolic compounds like BPA, and is considered to be genetically polymorphic (Raftogianis et al 1997;Nowell et al 2000;Carlini et al 2001) in human.…”

Section: Introductionmentioning

confidence: 99%

Biological Monitoring of Bisphenol A in a Korean Population

Yang

Kim

Lee

et al. 2003

Archives of Environmental Contamination and Toxicology

View full text Add to dashboard Cite

Abstract.To conduct proper biological monitoring of environmental exposure to bisphenol A (BPA), the variation in host susceptibility need to be investigated. For this purpose, we studied effects of genetic polymorphism in sulfotransferase (SULT) 1A1 on urinary BPA, a biomarker for BPA exposure, in 73 Koreans (male, 34; female, 39; age, 48.9 Ϯ 11.9 yrs). We used reverse phase-HPLC/FD for analysis of urinary BPA and obtained information from each subject on lifestyle, environment, and potential exposure to BPA via food. The HPLC/FD method showed good reproducibility (CVs Ͻ 0.1) and a relatively sensitive detection limit of 0.012 g/L. These methods yielded a geometric mean of urinary BPA as 9.54 g/L (8.91 g/g creatinine), with a geometric standard deviation of 8.32 g/L. Among potential routes for BPA exposure, only "vinyl wrapping of microwave heating" indicated a borderline positive association with urinary BPA level ( p ϭ 0

show abstract

Section: Introductionmentioning

confidence: 99%

Biological Monitoring of Bisphenol A in a Korean Population

Yang

Kim

Lee

et al. 2003

Archives of Environmental Contamination and Toxicology

View full text Add to dashboard Cite

show abstract

“…Elucidation of the metabolism and fate of nonylphenol is important for estimating the risks of the chemical for animals. Xenoestrogens such as bisphenol A and diethylstilbestrol have been shown to be conjugated with glucuronic acid by a UDPglucuronosyltransferase isoform, UGT2B1, in the rat liver (Yokota et al, 1999). Nonylphenol has also been reported to be glucuronidated extensively in the liver of animals such as rainbow trout (Lewis and Lech, 1996;Coldham et al, 1998; Thibaut et al, 1998a,b) and rats (Moffat et al, 2001;Yokota et al, 2002).…”

mentioning

confidence: 99%

“…cDNA of rat UDPglucuronosyltransferase isoform UGT2B1 was obtained by reverse transcriptase-polymerase chain reaction and expressed in yeast AH22 cells as previously described (Yokota et al, 1999). Nonylphenol glucuronidation was performed using yeast microsome-expressed UGT2B1, and the resultant glucuronide conjugate was analyzed by HPLC as described previously (Yokota et al, 1999).…”

mentioning

confidence: 99%

“…The bile was dissolved in 40-fold 50% acetonitrile, and perfusate was diluted with an equal volume of acetonitrile; then, the perfusate mixtures were centrifuged for 10 min at 10,000g. The supernatant fractions were analyzed by HPLC (Shimadzu, Tokyo, Japan) according to the method described previously (Yokota et al, 1999;Inoue et al, 2001). Alkylphenols and its metabolites were eluted from HPLC by 75% acetonitorile solution (acetonitrile/water/acetic acid, 75:25:0.1) for nonylphenol, 60% solution for hexylphenol, 50% solution for butylphenol, and 35% solution for ethylphenol.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Glucuronidation and Excretion of Nonylphenol in Perfused Rat Liver

Daidoji¹,

Inoue²,

Kato³

et al. 2003

Drug Metab Dispos

Self Cite

View full text Add to dashboard Cite

This article is available online at http://dmd.aspetjournals.org ABSTRACT:Nonylphenol, an environmental estrogenic chemical, is reported to have adverse effects on the reproductive organs of animals. In this study, the metabolism of nonylphenol and that of other alkylphenols in the rat liver was investigated using liver perfusion. Alkylphenols (nonylphenol, hexylphenol, butylphenol, and ethylphenol) were glucuronidated by rat liver microsomes. Nonylphenol was found to be conjugated with glucuronic acid by an isoform of UDP-glucuronosyltransferase, UGT2B1, expressed in yeast AH22 cells. However, when nonylphenol was perfused into rat liver in situ, it was difficult for free nonylphenol and conjugated metabolite to be excreted into the bile or vein, and most of the perfused nonylphenol remained free and as a glucuronide conjugate in the liver tissue, even after 1 h of perfusion. After 1 h of perfusion of the other alkylphenols, most of them were excreted into the bile as glucuronides. Ethylphenol, which has the shortest alkyl chain, was excreted rapidly into both the bile and vein; however, the excretion rates of alkylphenols having longer alkyl chains tended to be slow. MRP-2-deficient Eisai hyperbilirubinemic rats could not secrete alkylphenol-glucuronides into the bile, indicating that alkylphenolglucuronides are transported by MRP-2 to the bile in normal Sprague-Dawley rats. The results indicate that the kinetics of excretion of alkylphenol-glucuronides into the bile or vein depends on the length of alkyl chain and suggest that nonylphenol-glucuronide formed in the liver cannot be transported by MRP-2.Environmental estrogenic chemicals such as bisphenol A and nonylphenol, which are contained in many industrial products, can be detected in foods, tap water, and many environmental materials. Nonylphenol is used in a wide variety of detergents and plastics and has been reported to be environmentally persistent (White et al., 1994). The mean daily oral intake of nonylphenol by humans is estimated to be 0.16 mg/day (Muller et al., 1998). Nonylphenol has been shown to be a possible endocrine disrupter due to its estrogenic effects in MCF7 cell proliferation assays (Soto et al., 1991), binding assays to the estrogen receptor (White et al., 1994) and uterotropic assays in mice (Shelby et al., 1996). Exposure of male rainbow trout (Oncorhynchus mykiss) to four different alkylphenolic chemicals, including nonylphenol, resulted in synthesis of vitellogenin, a process normally dependent on endogenous estrogens, and a concomitant inhibition of testicular growth (Jobling et al., 1996). Male and female ratios of Japanese medaka (Oryzias latipes) in a control group (2:1) and a 100 g/l nonylphenol treatment group (1:2) were reported to be significantly different (Gray and Metcalfe, 1997). Early neonatal exposure to nonylphenol has been reported to cause dysfunction of postpubertal reproductive function in female rats as well as disrupted development of gonads in male and female rats (Nagao et al., 2000). It has also been repor...

show abstract

“…EDCs have been detected in human adipose tissue and biological fluids such as: sera [5], urine [6], milk [7], and amniotic fluid [8].…”

Section: Szkolenie Podyplomowementioning

confidence: 99%

Stanowisko Polskiego Towarzystwa Endokrynologicznego dotyczące związków endokrynnie czynnych (EDC)

Rutkowska

Rachoń

Milewicz

et al. 2015

Endokrynologia Polska

View full text Add to dashboard Cite

With the reference to the position statements of the Endocrine Society, the Paediatric Endocrine Society, and the European Society of Paediatric Endocrinology, the Polish Society of Endocrinology points out the adverse health effects caused by endocrine disrupting chemicals (EDCs) commonly used in daily life as components of plastics, food containers, pharmaceuticals, and cosmetics. The statement is based on the alarming data about the increase of the prevalence of many endocrine disorders such as: cryptorchidism, precocious puberty in girls and boys, and hormone-dependent cancers (endometrium, breast, prostate). In our opinion, it is of human benefit to conduct epidemiological studies that will enable the estimation of the risk factors of exposure to EDCs and the probability of endocrine disorders. Increasing consumerism and the industrial boom has led to severe pollution of the environment with a corresponding negative impact on human health; thus, there is great necessity for the biomonitoring of EDCs in Poland. StreszczenieW nawiązaniu do opublikowanych ostatnio stanowisk Towarzystwa Endokrynologicznego (Endocrine Society), Towarzystwa Endokrynologii Pediatrycznej (Pediatric Endocrine Society) oraz Europejskiego Towarzystwa Endokrynologii Pediatrycznej (European Society of Pediatric Endocrinology), Polskie Towarzystwo Endokrynologiczne (PTE) zwraca uwagę na negatywne skutki zdrowotne spowodowane ekspozycją na związki endokrynnie czynne (EDC, endocrine disrupting chemicals) używane w przemyśle jako składowe plastików, opakowań żywności, leków oraz kosmetyków. Postępująca urbanizacja, industrializacja i konsumpcjonizm prowadzą do zwiększonego skażenia środowiska, które wpływa negatywnie na organizmy żywe, w tym również na ludzkie zdrowie. Obecnie znanych jest ponad 800 związków, które wykazują zdolność zaburzania czynności układu dokrewnego. Narastająca częstość występowania przypadków zaburzeń endokrynnych, zaburzeń rozwoju narządów płciowych, zaburzeń metabolicznych zwraca szczególną uwagę na potencjalną rolę czynników środowiskowych. Stanowisko PTE zostało sprowokowane alarmującymi danymi o wzroście częstości występowania: zaburzeń płodności, wnętrostwa, przedwczesnego dojrzewania płciowego dziewcząt i chłopców, nowotworów hormonozależnych, w tym raka endometrium, sutka, gruczołu krokowego, jajnika i jąder. W opinii autorów konieczne jest przeprowadzenie w Polsce reprezentatywnych, długoterminowych badań epidemiologicznych pozwalających na ocenę związku pomiędzy ekspozycją na EDC a występowaniem zaburzeń czynności gruczołów wydzielania wewnętrznego. Niezwykle ważne wydaje się stworzenie wielodyscyplinarnej grupy badawczej. Uzyskane wyniki po przedstawieniu przedstawicielom rządu, mogłyby umożliwić wprowadzenie stosownych rozporządzeń prawnych.

show abstract

Glucuronidation of the environmental oestrogen bisphenol A by an isoform of UDP-glucuronosyltransferase, UGT2B1, in the rat liver

Cited by 153 publications

References 35 publications

Biological Monitoring of Bisphenol A in a Korean Population

Biological Monitoring of Bisphenol A in a Korean Population

Glucuronidation and Excretion of Nonylphenol in Perfused Rat Liver

Stanowisko Polskiego Towarzystwa Endokrynologicznego dotyczące związków endokrynnie czynnych (EDC)

Contact Info

Product

Resources

About