Highly Efficient Preparation of Bisphenol A Glucuronide†

doi:10.7503/cjcu20130613

Abstract

Abstract:

Bisphenol A(BPA), an industrial chemical, has been present in many hard plastic bottles, metal-based food and beverage cans. Many governments are trying to reduce the human exposure to BPA because it is really a readily accessible toxin for human. BPA can be extensively metabolized to bisphenol A-β-O-glucuronide(BPA-G) by UDP-glucuronosyltransferases(UGTs), thus the biological activities of BPA-G should be studied intensively. However, the studies on BPA-G are very limited due to the difficulty for preparation of BPA-G. In this work, the BPA-G was prepared using BPA as the starting material and rat liver microsomes(RLM) as the enzyme source. A series of orthogonal experiments was designed and performed to determine the optimal reaction conditions for BPA glucuronidation in RLM. After incubation under the optimal reaction conditions, the conversion of BPA was higher than 98%. A unique solid-phase extraction column(SPE) packed with C₁₈WAX was used to enrich and purify the product BPA-G with high yield. Finally, the product was identified by both ESI-MS and NMR techniques.

Key words: Bisphenol A, Rat liver microsome, Bisphenol A-β-O-glucuronide, Solid-phase extraction

TrendMD:

YANG Gang, ZHU Liangliang, LÜ Xia, WU Dachang, XIA Yangliu, MA Xiaochi, XIN Yi, HOU Jie. Highly Efficient Preparation of Bisphenol A Glucuronide^†[J]. Chem. J. Chinese Universities, 2014, 35(2): 314.

Figures/Tables 8

References 18

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No.	Substrate concentration^a/(mmol·L^-1)	RLM concentration^b/(mg·mL^-1)	Incubation time^c/h
1	0.5	0.2	1
2	1.0	0.4	2
3	1.5	0.6	4

No.	Substrate concentration^a/(mmol·L^-1)	RLM concentration^b/(mg·mL^-1)	Incubation time^c/h
1	0.5	0.2	1
2	1.0	0.4	2
3	1.5	0.6	4

No.	A	B	C	D(Blank)	Experiment scheme
1	1	1	1	1	A1B1C1
2	1	2	2	2	A1B2C2
3	1	3	3	3	A1B3C3
4	2	1	2	3	A2B1C2
5	2	2	3	1	A2B2C3
6	2	3	1	2	A2B3C1
7	3	1	3	2	A3B1C3
8	3	2	1	3	A3B2C1
9	3	3	2	1	A3B3C2

No.	A	B	C	D(Blank)	Experiment scheme
1	1	1	1	1	A1B1C1
2	1	2	2	2	A1B2C2
3	1	3	3	3	A1B3C3
4	2	1	2	3	A2B1C2
5	2	2	3	1	A2B2C3
6	2	3	1	2	A2B3C1
7	3	1	3	2	A3B1C3
8	3	2	1	3	A3B2C1
9	3	3	2	1	A3B3C2

No.	A	B	C	D(Blank)	Conversion(%)
1	1	1	1	1	92.7
2	1	2	2	2	94.4
3	1	3	3	3	91.8
4	2	1	2	3	98.9
5	2	2	3	1	96.2
6	2	3	1	2	85.1
7	3	1	3	2	84.5
8	3	2	1	3	72.2
9	3	3	2	1	89.3