生物样品中烷基酚类内分泌干扰物的前处理和分析方法
Pretreatment and analytical methods of alkylphenolic endocrine disrupters in biological samples
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摘要: 烷基酚类化合物具有与天然雌激素相似的结构,是一类典型的内分泌干扰物,被广泛应用于表面活性剂、纺织印染、橡胶塑料、油溶性酚醛树脂等领域,已经在环境介质中被广泛检测到.由于酚基类物质通常具有亲脂性和生物累积性,因此,生物样品中该类化合物的检测成为健康风险评价的关键.本文对近年来生物样品(生物组织、血液、尿液等)中烷基酚类物质的前处理技术与检测方法进行了综述,并对未来的发展趋势进行了展望.Abstract: Alkylphenolic compounds have similar structures to natural estrogen hormones, and are typical endocrine disrupters. They are widely used as surfactants, textile dyeing and finishing materials, rubbers and plastics, oil-soluble phenolic resins et al, and have been detected in various environmental compartments. Determination of alkylphenolic conpounds in biological samples is a key to estimate the associated health risk due to lipophilicity and bioaccumulation. The aim of this review was to present the pretreatment and analytical methods of alkylphenolic compounds in biological samples(including urine, blood, bile et al). In addition, outlook on the future developments was also presented.
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Key words:
- alkylphenol /
- biological samples /
- pretreatment /
- analytical methods
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[1] Bredhult C,Bäcklin B M,Olovsson M.Effects of some endocrine disruptors on the proliferation and viability of human endometrial endothelial cells in vitro[J]. Reproductive Toxicology, 2007,23(4):550-559 [2] Murray T J,Lea R G,Abramovich D R, et al. Endocrine disrupting chemicals:effects on human male reproductive health[J]. Early pregnancy,2001.2(5):80-112 [3] Chen Y J,Cheng F X,Sun L, et al. Computational models to predict endocrine-disrupting chemical binding with androgen or oestrogen receptors[J]. Ecotoxicology and Environmental Safety, 2014,110:280-287 [4] 严炜,林金明. 雌激素类内分泌干扰物的液相色谱-质谱分析样品前处理方法[J]. 分析化学,2010,38(4):598-606 [5] 林福华,邱宁宁,黄晓佳,等. 搅拌棒固相萃取与液相色谱联用测定水样品中烷基酚类污染物[J]. 分析化学,2010,01:67-71 [6] Kawaguchi M,Ito R,Sakui N, et al. Stir-bar-sorptive extraction, with in-situ deconjugation,and thermal desorption with in-tube silylation, followed by gas chromatography-mass spectrometry for measurement of urinary 4-nonylphenol and 4-tert-octylphenol glucuronides[J].Anal Bioanal Chem,2007,388:391-398 [7] Li X,Ying G G,Zhao J L, et al. 4-Nonylphenol, bisphenol-A and triclosan levels in human urine of children and students in China, and the effects of drinking these bottled materials on the levels[J]. Environment International, 2013,52:81-86 [8] Kuklenyik Z,Ekong J,Cutchins C D, et al.Simultaneous measurement of urinary bisphenol a and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry[J]. Analytical Chemistry, 2003,75:6820-6825 [9] Chen R,Yin P,Zhao L, et al. Spatial-temporal distribution and potential ecological risk assessment of nonylphenol and octylphenol in riverine outlets of Pearl River Delta, China[J]. Jouranal of environmental sciences, 2014,26:2340-2347 [10] Cespedes R.,Lacorte S.,Ginegreda A, et al.Occurence and fate of alkylphenols and alkylphenol ethoxylates in sewage treatment plants and impact on receiving waters along the Ter River(Catalonia, NE Spain).Environmental Pollution,2008,153:384-392 [11] Zgoła-Grzes'kowiak A,Grzes'kowiak T,Rydlichowski R, et al. Determination of nonylphenol and short-chained nonylphenol ethoxylates in drain water from an agricultural area[J]. Chemosphere, 2009,75:513-518 [12] Brix R,Postigo C,González S, et al. Analysis and occurrence of alkylphenolic compoundsand estrogens in a European river basin and an evaluationof their importance as priority pollutants[J]. Analytical and Bioanalytical Chemistry, 2010,396:1301-1309 [13] Salgueiro-González N,Turnes-Carou I,Muniategui-Lorenzo S, et al.Membrane assisted solvent extraction coupled with liquid chromatography tandem mass spectrometry applied to the analysis of alkylphenols in water samples[J].Journal of Chromatography A,2013,1281:46-53 [14] 侯绍刚,徐建,汪磊,等.黄河(兰州段)水环境中壬基酚及壬基酚聚氧乙烯醚污染的初步研究[J]. 环境化学,2005,24(3):250-253 [15] 丁洁,张圣虎,刘济宁,等.液相色谱-串联质谱法测定污水处理厂水样中双酚A、四溴双酚A及烷基酚类化合物[J]. 色谱,2014,32(5):529-534 [16] Guenther K, Heinke V, Thiele B, et al. Endocrine disrupting nonylphenols are ubiquitous in food[J]. Environmental Science and Technology, 2002,36:1676-1680 [17] Lu YY,Chen M L,Sung F C, et al Daily intake of 4-nonylphenol in Taiwanese. Environment International,2007,33:903-910 [18] Brock J W,Yoshimura Y,Barr J R. Measurement of bisphenol A levels in human urine[J]. Journal of Exposure Analysis and Evironment Epidemiology, 2001,11:323-328 [19] Shangari N,Chan T S,Peter J,et al. Sulfation and glucuronidation of phenols:Implications in coenyzmeq metabolism[J].Methods in Enzymology, 2005,400:342-359 [20] Del Olmo M,Zafra A,Suarez B,et al.Use of solid-Phase microextraetion followed by on-column silylation for determining chlorinated bisphenol A in human Plasma by gas chromatography-mass spectrometry[J]. Journal of Chromatography B,2005,817(2):167-172 [21] Ye X Y,Kuklenyik Z,Larry L, et al.Quantification of urinary conjugates of bisphenol A,2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry[J]. Analytical Biochemistry, 2005,383:638-644 [22] Genuis S J,Beesoon S,Birkholz D, et al. Human excretion of bisphenol a:blood, urine, and sweat (BUS) study[J]. Journal of Environmental and Public Health, 2012,1-10 [23] Schoringhumer K,Cichna-Marki M.Sample clean-up with sol-gel enzyme and immunoaffinity columns for the determination of bisphenol A in human urine[J].Journal of Chromatography B,2007,850:361-369 [24] Kuroda N,Kinoshita Y,Sun Y, et al.Measurement of bisphenol A levels in human blood serum and ascitic fluid by HPLC using a fluorescent labeling reagent[J].Journal of Pharmaceutical and Biomedical Analysis,2003,30(6):1743-1749 [25] 郑力行,石峻岭,周志俊. 高效液相色谱法测定血清中的双酚A[J]. 中华预防医学杂志,2003,37(6):450-451 [26] 肖全伟,黎源倩,张浩,等. 高效液相色谱法测定大鼠血清中4-壬基酚和双酚A[J]. 四川大学学报(医学版),2004,35(2 ):271-273
[27] 郭志磊,范捷. 固相萃取和蛋白沉淀法在高效液相色谱法测定万古霉素血药浓度中的比较[J]. 中国医院药学杂志,2013,33(9):745-747 [28] 吴同俊,郑力行,吴强恩,等. 酶水解-高效液相色谱法测定人血清中双酚A[J]. 中国工业医学杂志,2006,19(2):70-73 [29] Abend A M,Chung L,McCollum D G, et al. Development and validation of an automated extraction method (accelerated solvent extraction and a reverse-phase HPLC analysis method for assay of ivermectin in a meat-based chewable formulation[J]. Journal of Pharmaceutical and Biomedical Analysis, 2003,31(6):1177-1183 [30] 徐振东,顾娟红,黄丽娟,等. 加速溶剂萃取-快速液相色谱法测定纺织品中烷基苯酚和烷基苯酚聚氧乙烯醚[J]. 分析试验室,2012,31(8):112-115 [31] 肖晶,邵兵,吴永宁,等. HPLC-FL法检测尿液中类雌激素双酚A和烷基酚[J]. 中国食品卫生杂志,2008,20(2):111-113 [32] Shin B S,Park K L,Han S Y, et al.Sensitive micro-sample analysis of bisphenol A in serum by high-performance liquid chromatography with fluorescence Detection[J]. Chromatographia, 2001,53:669-672 [33] Jonkers N, Knepper T P, de Voogt P. Aerobic biodegradation studies of nonylphenol ethoxylates in river water using liquid chromatographyelectrospray tandem mass spectrometry[J]. Environmental Science and Technology, 2001, 35:335-340 [34] Salgueiro-González N,Turnes-Carou I,Muniategui-Lorenzo S, et al.Membrane assisted solvent extraction coupled with liquid chromatography tandem mass spectrometry applied to the analysis of alkylphenols in water samples[J].Journal of Chromatography A, 2013,1281:46-53 [35] Ye X Y,Kuklenyik Z,Larry L, et al.Quantification of urinary conjugates of bisphenol A,2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry[J]. Analytical Biochemistry, 2005,383:638-644 [36] 夏同伟,刘良坡,张文静,等. 高效液相色谱-串联质谱法测定人尿液中5种酚类内分泌干扰物[J].分析测试学报,2013,32(2):211-217 [37] Xiao J,Shao B,Wu X Y, et al.A Study on bisphenol A, nonylphenol, and octylphenol in human urine amples detected by SPE-UPLC-MS[J].Biomed Environ Sci,2011,24(1):40-46 [38] 鲍慧惠,盛杰,许媛媛,等. 血清中游离型双酚A的固相萃取-同位素内标-高效液相色谱串联质谱测定法[J]. 环境与健康杂志,2014,31(1):44-46 [39] 赵永纲,陈晓红,范建中. 超快速液相色谱-串联质谱法测定牛蛙全血中3种酚类环境雌激素[J]. 中国卫生检验,2012,22(9):2007-2010 [40] Pedersen S N,Lindholst C.Quantification of the xenoestrogens 4-tert.-octylphenol and bisphenol A in water and in fish tissue based on microwave assisted extraction, solid-phase extraction and liquid chromatography-mass spectrometry[J]. Journal of Chromatography A, 1999,864(1):17-24 [41] Choi J-H,Lamshoft M,Zuhlke S, et al. Determination of sedatives and adrenergic blockers in blood meal using accelerated solvent extraction and Orbitrap mass spectrometry[J]. Journal of Chromatography A, 2012,1260:111-119 [42] Tavazzil S,Benfenati E,Barcelo D. Accelerated solvent extraction then liquid chromatography coupled with mass spectrometry for determination of 4-t-Octylphenol, 4-Nonylphenols, and bisphenol A in fish liver[J]. Chromatographia, 2002,56:463-467 [43] Kuklenyik Z,Ekong J,Cutchins C D, et al.Simultaneous measurement of urinary bisphenol A and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry[J]. Analytical Chemistry, 2003, 75:6820-6825 [44] Kawaguchi M,Ito R,Sakui N, et al. Stir-bar-sorptive extraction, with in-situ deconjugation,and thermal desorption with in-tube silylation, followed by gas chromatography-mass spectrometry for measurement of urinary 4-nonylphenol and 4-tert-octylphenol glucuronides[J]. Analytical Biochemistry, 2007,388:391-398 [45] Del Olmo M,Zafra A,Suarez B,et al.Use of solid-Phase microextraetion followed by on-column silylation for determining chlorinated bisphenol A in human Plasma by gas chromatography-mass spectrometry[J]. Journal of Chromatography B, 2005,817(2):167-172 [46] [47] Mao L S,Sun C J,Zhang H, et al. Determination of environmental estrogens in human urine by high performance liquid chromatography after flurescent derivatization with p-nitrobenzoyl chloride[J]. Analytica Chimica Acta, 2004,522(2):241-246 [48] 张宏,毛炯,孙成均,等.气相色谱-质谱法测定尿及河底泥中的环境雌激素[J]. 色谱,2003,21(5):451-455 [49] Kawaguchi M,Ito R,Hayastu Y, et al. Stir bar sorptive extraction with in situ de-conjugation and thermal desorption gas chromatography-mass spectrometry for measurement of 4-nonylphenol glucuronide in human urine sample[J]. Journal of Pharmaceutical and Biomedical Analysis, 2006,40(1):82-87 [50] Kawaguchia M,Inouea K,Yoshimura M, et al.Determination of 4-nonylphenol and 4-tert.-octylphenol in water samples by stir barsorptive extraction and thermal desorption-gas chromatography-mass spectrometry[J]. Analytica Chimica Acta,2004,505(2):217-222 [51] Yang J,Li H Y,Ran Y, et al.Distribution and bioconcentration of endocrine disrupting chemicals in surface water and fish bile of the Pearl River Delta, South China[J]. Chemosphere, 2014,107:439-446 [52] 王世玉,刘菲,吴文勇,等. 影响 12 种壬基酚同分异构体液液萃取效率的因素研究[J]. 岩矿测试,2014,33(4):570-577 [53] Chen G W,Ding W H,Ku H Y, et al. Alkylphenols in human milk and their relations to dietary habits in central Taiwan[J].Food and Chemical Toxicology,2010,48:1939-1944 [54] Pirard C,Sagot C,Deville M, et al. Urinary levels of bisphenol A,triclosan and 4-nonyphenol in a general Belgian population[J]. Environmental International, 2012,48:78-83 [55] Huang Y F,Wang P W,Huang L W, et al.Nonylphenol in pregnant women and their matching fetuses:Placental transfer and potential risks of infants[J]. Environmental Research, 2014,134:143-148 [56] BelardiR P, Pawliszyn J. The application of chemically modified fused silica fibers in the extraction of organics from water matrix samples and their rapid transfer to capillary columns[J]. Water Pollut Res J Can, 1989,24:179-191 [57] Kataoka H,Saito K. Recent advances in SPME techniques in biomedical analysis[J]. Journal of Pharmaceutical and Biomedical Analysis, 2011,54(5):926-950 [58] Theodoridis G,Koster E H M,Jong G J. Solid-phase microextraction for the analysis of biological samples[J]. Journal of Chromatography B, 2000,745(1):49-82 [59] 张鹤小.固相微萃取高效液相色谱法测定工业污水中酚类环境激素[D].沈阳:沈阳师范大学硕士学位论文,2013 [60] Queriroz M E C,Melo L P. Selective capillary coating materials for in-tube solid-phase microextraction coupled to liquid chromatography to determine drugs and biomarkers in biological samples:A review[J]. Analytica Chimica Acta, 2014,826:1-11 [61] Yang L H,Luan T G,Lan C Y. Solid-phase microextraction with on-fiber silylation for simultaneous determinations of endocrine disrupting chemcals and steriod hormones by gas chromatography-mass spectrometry[J]. Journal of Chromatography A, 2006,1104(1/2):23-32. [62] Baltussen E,Sandra P,David F, et al. Stir-bar sorptive extraction(SBSE),A novel extraction technique for aqueous sample theory and principles[J]. Journal of Microcolumn Separations, 1999,11(10):737-7471 [63] Kawaguchia M,Inouea K,Yoshimura M, et al.Determination of 4-nonylphenol and 4-tert.-octylphenol in water samples by stir bar sorptive extraction and thermal desorption-gas chromatography-mass spectrometry[J]. Analytica Chimica Acta, 2004,505(2):217-222 [64] Nogueira J M F. Novel sorption-based methodologies for static microextraction analysis:A review on SBSE and related techniques[J]. Analytica Chimica Acta, 2012,757:1-10 [65] Zeng W,Xu Y,Constanzer M, et al. Determination of sitagliptinin human plasma using protein precipitation and tandem mass spectrometry[J]. J Chromatogr B, 2010,878(21):1817-1823 [66] 赵永纲,陈晓红,姚姗姗,等. 分散固相萃取-超快速液相色谱-串联质谱法测定牛蛙全血中6种酚类环境雌激素[J]. 色谱,2012,30(7):665-671 [67] Asimakopoulos A G,Thomaidis N S. Bisphenol A,4-t-octylphenol,and 4-nonylphenol determination in serum by Hybrid Solid Phase Extraction-Precipitation Technology technique tailored to liquid chromatography-tandem mass spectrometry[J]. Journal of Chromatography B, 2015,986-987:85-93 [68] Casas M E,Hansen M,Krogh K A, et al. Analytical sample preparation strategies for determination of antimalarial drugs in human whole blood,plasma and urine[J]. Journal of Chromatography B, 2014,962(1):109-131 [69] Pucci V,Palma S D,Alfieri A, et al. A novel strategy for reducing phospholipids-based matrix effect in LC-ESI-MS bioanalysis by means of HybridSPE[J]. Journal of Pharmaceutical and Biomedical Analysis, 2009,50(5):867-871 [70] 吴明红,潘辰苑,杨明,等.鱼体胆汁中壬基酚和双酚A的分析方法[J]. 上海大学学报,2013,19(4):423-428 [71] Fenlon K A,Johnson A C,Tyler C R et al. Gas-liquid chromatography-tandem mass spectrometry methodology for the quantitation of estrogenic contaminants in bile of fish exposed to wastewater treatment works effluents and from wild populations[J]. Journal of Chromatography A, 2010,1217:112-118 [72] 卢彦芳,张福成,安静,等. 微波辅助萃取应用研究进展[J]. 分析科学学报,2011,27(2):246-252 [73] Leufroy A,Noel L,Dufailly V, et al. Determination of seven arsenic species in seafood by ion exchange chromatography coupled to inductively coupled plasma-mass spectrometry following microwave assisted extraction:Method validation and occurrence data[J].Talanta,2011,83(5):770-779 [74] Prado L S,Jares C G,Llompart M. Microwave-assisted extraction:Application to the determination of emerging polutants in solid samples[J]. Journal of Chromatography A, 2010,1217(16):2390-2414 [75] Choi J H,Lamshoft M,Zuhlke S, et al. Determination of sedatives and adrenergic blockers in blood meal using accelerated solvent extraction and Orbitrap mass spectrometry[J]. Journal of Chromatography A, 2012,1260:111-119 [76] Sun H W,Ge X H,Lv Y K, et al. Application of accelerated solvent extraction in analysis of organic contaminants,bioactive and nutritional compounds in food and feed[J]. Journal of Chromatography A, 2012,1237(11):1-23 [77] Shao B,Han H,Li D M, et al. Analysis of alkylphenol and bisphenol A in meat by accelerated solvent extraction and liquid chromatography with tandem mass spectrometry[J]. Food Chemistry, 2007,105(3):1236-1241 [78] Barker S A,Long A R,Short C R. Isolation of durg residues from tissues by solid phase dispersion[J]. Journal of Chromatography A, 1989,475(2):353-361 [79] Barker S A. Matrix solid phase dispersion (MSPD)[J]. Journal of Biochemical and Biophysical Methods, 2007,70(2):151-162 [80] Capriotti A L,Cavaliere C,Giansanti P, et al. Recent developments in matrix solid-phase dispersion extraction[J]. Journal of Chromatography A, 2010,1217(16):2521-2532 [81] Shao B,Han H,Tu X M, et al. Analysis of alkylphenol and bisphenol A in eggs and milk by matrix solid phase dispersion extraction and liquid chromatography with tandem mass spectrometry[J]. Journal of Chromatography B, 2007,805(1/2):412-416 [82] Niki,Maragou,Eugenia, et al. Determination of bisphenol A in milk by solid phase extraction and liquid chromatography-mass spectrometry[J]. Journal of Chromatography A, 2006,1129(2):165-173 [83] Rice,Afonso S,Rosale L, et al. Alkylphenol and alkylphenol-ethoxylates in carp,water and sediment from the Cuyahoga River,Ohio[J]. Environmental Science&Technology, 2003,37(17):3747-3754 [84] Ferrara,Ademollo,Orr, et al.Alkylphenols in adipose tissues of Italian population[J]. Chemosphere, 2011,82(7):1044-1049 [85] 杜志辉,李森林,高志贤,等. 壬基酚免疫层析快速检测试纸条的研制[J]. 解放军预防医学,2007,25(4):238-241 [86] Lina W C,Wang S L,Cheng C Y, et al. Determination of alkylphenol residues in breast and commercial milk by solid-phase extraction and gas chromatography-mass spectrometry[J]. Food Chemistry, 2009,114:753-757 [87] Kawaguchia M,Inoue K,Sakui N, et al. Stir bar sorptive extraction and thermal desorption gas chromatography-mass spectrometry for the measurement of 4-nonylphenol and 4-tert-octylphenol in human biological samples[J]. Journal of Chromatography B, 2004,799:119-125 [88] Inoue K,Kawaguchi M,Okada F, et al.Measurement of 4-nonylphenol and 4-tert-octylphenol in human urine by column-switching liquid chromatograph-mass spectrometry[J]. Analytica Chimica Acta, 2003,486:41-50 [89] Ye X Y,Kuklenyik Z, Larry L, et al. Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry[J]. Journal of Chromatography B, 2006,831:110-115 -

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