壬基酚异构体的组成、环境行为及毒性效应研究进展

杨彦, 高源, 马盛韬, 龚剑, 余应新. 壬基酚异构体的组成、环境行为及毒性效应研究进展[J]. 生态毒理学报, 2023, 18(1): 206-216. doi: 10.7524/AJE.1673-5897.20220214002
引用本文: 杨彦, 高源, 马盛韬, 龚剑, 余应新. 壬基酚异构体的组成、环境行为及毒性效应研究进展[J]. 生态毒理学报, 2023, 18(1): 206-216. doi: 10.7524/AJE.1673-5897.20220214002
Yang Yan, Gao Yuan, Ma Shengtao, Gong Jian, Yu Yingxin. Composition, Isomer-specific Occurrences, Environmental Fate and Toxicity of Nonylphenols: A Review[J]. Asian Journal of Ecotoxicology, 2023, 18(1): 206-216. doi: 10.7524/AJE.1673-5897.20220214002
Citation: Yang Yan, Gao Yuan, Ma Shengtao, Gong Jian, Yu Yingxin. Composition, Isomer-specific Occurrences, Environmental Fate and Toxicity of Nonylphenols: A Review[J]. Asian Journal of Ecotoxicology, 2023, 18(1): 206-216. doi: 10.7524/AJE.1673-5897.20220214002

壬基酚异构体的组成、环境行为及毒性效应研究进展

    作者简介: 杨彦(1984—),女,博士,副教授,研究方向为场地特征污染物的筛查、识别与健康风险评估,E-mail:yangyan1209@gdut.edu.cn
    通讯作者: 马盛韬, E-mail: mast@gdut.edu.cn
  • 基金项目:

    国家自然科学基金资助项目(41907299,42077321);国家重点研发计划(2018YFC1801102);化学与精细化工广东省实验室科研启动项目(2032008)

  • 中图分类号: X171.5

Composition, Isomer-specific Occurrences, Environmental Fate and Toxicity of Nonylphenols: A Review

    Corresponding author: Ma Shengtao, mast@gdut.edu.cn
  • Fund Project:
  • 摘要: 壬基酚(NPs)是一类典型的环境内分泌干扰物,具有较强的亲脂性,在土壤及沉积物等环境介质中难降解,并在生物体内具有蓄积性和高毒性,被列入我国“十四五”新污染物管控名单。NPs理论上存在211种同分异构体,而工业品NPs则是由50~80种同分异构体组成的混合物。已有充分证据显示NPs的环境行为及毒性效应呈异构体特异性差异,因此,必须从异构体分子水平上厘清NPs的环境行为、人体暴露及潜在毒性效应等,从而更精准地评估及预测其生态与健康风险。本文归纳了近些年国内外学者针对NPs同分异构体理化性质、工业品组成特征、环境行为及潜在的毒性效应等方面的研究进展,并对当前研究的瓶颈进行了梳理,展望了今后的主要研究方向。
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  • 李明姝, 刘征涛, 周俊丽. 内分泌干扰物壬基酚在环境中迁移转化的研究进展[J]. 环境化学, 2013, 32(7): 1212-1217

    Li M S, Liu Z T, Zhou J L. Advance in research on the transport and transformation of nonylphenol [J]. Environmental Chemistry, 2013, 32(7): 1212-1217 (in Chinese)

    Guruge K S, Horii Y, Yamashita N. Profiles of nonylphenol isomers in surface waters from Sri Lanka [J]. Marine Pollution Bulletin, 2011, 62(4): 870-873
    Telscher M J, Schuller U, Schmidt B, et al. Occurrence of a nitro metabolite of a defined nonylphenol isomer in soil/sewage sludge mixtures [J]. Environmental Science & Technology, 2005, 39(20): 7896-7900
    史雨薇, 蔡灵, 潘辰苑, 等. 海洋环境中新型雌激素污染特征研究进展[J]. 高校化学工程学报, 2019, 33(6): 1285-1302

    Shi Y W, Cai L, Pan C Y, et al. Research progress on emerging estrogenic pollutants in marine environment [J]. Journal of Chemical Engineering of Chinese Universities, 2019, 33(6): 1285-1302 (in Chinese)

    Geens T, Neels H, Covaci A. Distribution of bisphenol-A, triclosan and n-nonylphenol in human adipose tissue, liver and brain [J]. Chemosphere, 2012, 87(7): 796-802
    Chen M, Fan Z L, Zhao F R, et al. Occurrence and maternal transfer of chlorinated bisphenol A and nonylphenol in pregnant women and their matching embryos [J]. Environmental Science & Technology, 2016, 50(2): 970-977
    Ademollo N, Ferrara F, Delise M, et al. Nonylphenol and octylphenol in human breast milk [J]. Environment International, 2008, 34(7): 984-987
    Ringbeck B, Bury D, Hayen H, et al. Determination of specific urinary nonylphenol metabolites by online-SPE-LC-MS/MS as novel human exposure biomarkers [J]. Journal of Chromatography B, Analytical Technologies in the Biomedical and Life Sciences, 2021, 1177: 122794
    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
    Ieda T, Horii Y, Petrick G, et al. Analysis of nonylphenol isomers in a technical mixture and in water by comprehensive two-dimensional gas chromatography-mass spectrometry [J]. Environmental Science & Technology, 2005, 39(18): 7202-7207
    Kim Y S, Katase T, Horii Y, et al. Estrogen equivalent concentration of individual isomer-specific 4-nonylphenol in Ariake Sea water, Japan [J]. Marine Pollution Bulletin, 2005, 51(8-12): 850-856
    Chen M L, Lee H Y, Chuang H Y, et al. Association between nonylphenol exposure and development of secondary sexual characteristics [J]. Chemosphere, 2009, 76(7): 927-931
    Lu Z J, Gan J. Analysis, toxicity, occurrence and biodegradation of nonylphenol isomers: A review [J]. Environment International, 2014, 73: 334-345
    Acir I H, Guenther K. Endocrine-disrupting metabolites of alkylphenol ethoxylates—A critical review of analytical methods, environmental occurrences, toxicity, and regulation [J]. The Science of the Total Environment, 2018, 635: 1530-1546
    Guenther K, Kleist E, Thiele B. Estrogen-active nonylphenols from an isomer-specific viewpoint: A systematic numbering system and future trends [J]. Analytical and Bioanalytical Chemistry, 2006, 384(2): 542-546
    Chung S W C. The development of isomer-specific analysis of branched 4-nonylphenol in food for dietary exposure—A critical review of analytical methods and occurrence in foodstuffs [J]. Food Additives & Contaminants Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment, 2021, 38(5): 842-855
    王立恒. 壬基酚生产与市场分析[J]. 化学工业, 2014, 32(6): 36-39

    Wang L H. Nonylphenol production and market [J]. Chemical Industry, 2014, 32(6): 36-39 (in Chinese)

    Shan J, Wang T, Li C L, et al. Bioaccumulation and bound-residue formation of a branched 4-nonylphenol isomer in the geophagous earthworm Metaphire guillelmi in a rice paddy soil [J]. Environmental Science & Technology, 2010, 44(12): 4558-4563
    Sun J Q, Yang X D, Shen H, et al. Uptake and metabolism of nonylphenol in plants: Isomer selectivity involved with direct conjugation [J]. Environmental Pollution, 2021, 270: 116064
    虞斌, 边学森, 季荣. 4种具有α-季碳结构的对位壬基酚异构体的合成和表征[J]. 生态毒理学报, 2008, 3(1): 98-104

    Yu B, Bian X S, Ji R. Synthesis and characterization of four para-nonylphenol isomers containing a quaternary α-carbon [J]. Asian Journal of Ecotoxicology, 2008, 3(1): 98-104 (in Chinese)

    王世玉, 刘菲, 刘玉龙, 等. 气相色谱-质谱法检测地下水中12种对壬基酚同分异构体[J]. 分析化学, 2013, 41(11): 1699-1703

    Wang S Y, Liu F, Liu Y L, et al. Determination of 12 isomers of p-nonylphenol in groundwater by gas chromatography-mass spectrometry [J]. Chinese Journal of Analytical Chemistry, 2013, 41(11): 1699-1703 (in Chinese)

    Eganhouse R P, Pontolillo J, Gaines R B, et al. Isomer-specific determination of 4-nonylphenols using comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry [J]. Environmental Science & Technology, 2009, 43(24): 9306-9313
    Wheeler T F, Heim J R, LaTorre M R, et al. Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS [J]. Journal of Chromatographic Science, 1997, 35(1): 19-30
    Moeder M, Martin C, Schlosser D, et al. Separation of technical 4-nonylphenols and their biodegradation products by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry [J]. Journal of Chromatography A, 2006, 1107(1-2): 233-239
    Zhang C X, Eganhouse R P, Pontolillo J, et al. Determination of nonylphenol isomers in landfill leachate and municipal wastewater using steam distillation extraction coupled with comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry [J]. Journal of Chromatography A, 2012, 1230: 110-116
    Katase T, Okuda K, Kim Y S, et al. Estrogen equivalent concentration of 13 branched para-nonylphenols in three technical mixtures by isomer-specific determination using their synthetic standards in SIM mode with GC-MS and two new diasteromeric isomers [J]. Chemosphere, 2008, 70(11): 1961-1972
    Dupuis A, Migeot V, Cariot A, et al. Quantification of bisphenol A, 353-nonylphenol and their chlorinated derivatives in drinking water treatment plants [J]. Environmental Science and Pollution Research, 2012, 19(9): 4193-4205
    Liu N, Jin X W, Feng C L, et al. Ecological risk assessment of fifty pharmaceuticals and personal care products (PPCPs) in Chinese surface waters: A proposed multiple-level system [J]. Environment International, 2020, 136: 105454
    Zhao J L, Huang Z, Zhang Q Q, et al. Distribution and mass loads of xenoestrogens bisphenol A, 4-nonylphenol, and 4-tert-octylphenol in rainfall runoff from highly urbanized regions: A comparison with point sources of wastewater [J]. Journal of Hazardous Materials, 2021, 401: 123747
    殷伟, 范德玲, 汪贞, 等. 天津市地表水体与沉积物中7种高关注酚类化合物的污染特征与生态风险分析[J]. 生态毒理学报, 2020, 15(1): 230-241

    Yin W, Fan D L, Wang Z, et al. Pollution characteristics and ecological risks of 7 phenolic compounds of high concern in the surface water and sediments of Tianjin, China [J]. Asian Journal of Ecotoxicology, 2020, 15(1): 230-241 (in Chinese)

    Chen Q, Lan Y, Shi J, et al. Levels of NP and BPA in the Pearl River Estuary, China: Fluctuations with country policy changes over the past 40 years [J]. International Journal of Environmental Research and Public Health, 2019, 16(21): 4100
    周自坚, 刘文俊, 虢清伟, 等. 壬基酚聚氧乙烯醚在碱性印染废水中的降解[J]. 环境科学学报, 2015, 35(6): 1809-1816

    Zhou Z J, Liu W J, Guo Q W, et al. The degradation of nonylphenol ethoxylates in the alkaline dyeing wastewater [J]. Acta Scientiae Circumstantiae, 2015, 35(6): 1809-1816 (in Chinese)

    Fang Y X, Ying G G, Zhao J L, et al. Assessment of hormonal activities and genotoxicity of industrial effluents using in vitro bioassays combined with chemical analysis [J]. Environmental Toxicology and Chemistry, 2012, 31(6): 1273-1282
    Horii Y, Katase T, Kim Y S, et al. Determination of individual nonylphenol isomers in water samples by using relative response factor method [J]. Bunseki Kagaku, 2004, 53: 1139-1147
    Zhang H F, Zuehlke S, Guenther K, et al. Enantioselective separation and determination of single nonylphenol isomers [J]. Chemosphere, 2007, 66(4): 594-602
    Lu Z J, Gan J. Isomer-specific biodegradation of nonylphenol in river sediments and structure-biodegradability relationship [J]. Environmental Science & Technology, 2014, 48(2): 1008-1014
    Lu Z J, Reif R, Gan J. Isomer-specific biodegradation of nonylphenol in an activated sludge bioreactor and structure-biodegradability relationship [J]. Water Research, 2015, 68: 282-290
    Shan J, Jiang B Q, Yu B, et al. Isomer-specific degradation of branched and linear 4-nonylphenol isomers in an oxic soil [J]. Environmental Science & Technology, 2011, 45(19): 8283-8289
    Zhang H F, Spiteller M, Guenther K, et al. Degradation of a chiral nonylphenol isomer in two agricultural soils [J]. Environmental Pollution, 2009, 157(6): 1904-1910
    Wang Y F, Tian L L, Wang L H, et al. Degradation, transformation, and non-extractable residue formation of nitrated nonylphenol isomers in an oxic soil [J]. Environmental Pollution, 2021, 289: 117880
    Günther K, Räcker T, Böhme R. An isomer-specific approach to endocrine-disrupting nonylphenol in infant food [J]. Journal of Agricultural and Food Chemistry, 2017, 65(6): 1247-1254
    Kim Y S, Katase T, Sekine S, et al. Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography [J]. Chemosphere, 2004, 54(8): 1127-1134
    Routledge E J, Sumpter J P. Structural features of alkylphenolic chemicals associated with estrogenic activity [J]. The Journal of Biological Chemistry, 1997, 272(6): 3280-3288
    Preuss T G, Gehrhardt J, Schirmer K, et al. Nonylphenol isomers differ in estrogenic activity [J]. Environmental Science & Technology, 2006, 40(16): 5147-5153
    Saito H, Uchiyama T, Makino M, et al. Optical resolution and absolute configuration of branched 4-nonylphenol isomers and their estrogenic activities [J]. Journal of Health Science, 2007, 53(2): 177-184
    Zhang H F, Oppel I M, Spiteller M, et al. Enantiomers of a nonylphenol isomer: Absolute configurations and estrogenic potencies [J]. Chirality, 2009, 21(2): 271-275
    Roig B, Cadiere A, Bressieux S, et al. Environmental concentration of nonylphenol alters the development of urogenital and visceral organs in avian model [J]. Environment International, 2014, 62: 78-85
    Cheng Y, Shan Z J, Zhou J Y, et al. Effects of long-term 4-nonylphenol dietary exposure on reproductive ability of Japanese quails (Coturnix japonica) [J]. Environmental Science and Pollution Research International, 2019, 26(3): 2908-2917
    Uguz C, Varisli O, Agca C, et al. Effects of nonylphenol on motility and subcellular elements of epididymal rat sperm [J]. Reproductive Toxicology, 2009, 28(4): 542-549
    Liu X Z, Nie S P, Chen Y J, et al. Effects of 4-nonylphenol isomers on cell receptors and mitogen-activated protein kinase pathway in mouse Sertoli TM4 cells [J]. Toxicology, 2014, 326: 1-8
    Liu X Z, Li F X, Zhu Z L, et al. 4--phenol induces apoptosis and interrupts Ca2+ homeostasis via ROS pathway in Sertoli TM4 cells [J]. Environmental Science and Pollution Research, 2022, 29(35): 52665-52674
    Ying F, Ding C, Ge R, et al. Comparative evaluation of nonylphenol isomers on steroidogenesis of rat Leydig cells [J]. Toxicology in Vitro, 2012, 26(7): 1114-1121
    Celino-Brady F T, Petro-Sakuma C K, Breves J P, et al. Early-life exposure to 17β-estradiol and 4-nonylphenol impacts the growth hormone/insulin-like growth-factor system and estrogen receptors in Mozambique tilapia, Oreochromis mossambicus [J]. Aquatic Toxicology, 2019, 217: 105336
    De la Parra-Guerra A, Olivero-Verbel J. Toxicity of nonylphenol and nonylphenol ethoxylate on Caenorhabditis elegans [J]. Ecotoxicology and Environmental Safety, 2020, 187: 109709
    Yang W F, Gao X X, Wu Y X, et al. Chemical- and species-specific toxicity of nonylphenol and octylphenol to microalgae Chlorella pyrenoidosa and Scenedesmus obliquus [J]. Environmental Toxicology and Pharmacology, 2021, 81: 103517
    Xia H, Wang A Q, Zhang Y F, et al. Effects of nonylphenol on immune function of female Sprague-Dawley rats [J]. Toxicological & Environmental Chemistry, 2013, 95: 658-668
    Negishi T, Kawasaki K, Suzaki S, et al. Behavioral alterations in response to fear-provoking stimuli and tranylcypromine induced by perinatal exposure to bisphenol A and nonylphenol in male rats [J]. Environmental Health Perspectives, 2004, 112(11): 1159-1164
    中国生态环境部. 水质 9种烷基酚类化合物和双酚A的测定 固相萃取/高效液相色谱法: HJ 1192—2021 [S]. 北京: 中国生态环境部, 2021
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  • 收稿日期:  2022-02-14

壬基酚异构体的组成、环境行为及毒性效应研究进展

    通讯作者: 马盛韬, E-mail: mast@gdut.edu.cn
    作者简介: 杨彦(1984—),女,博士,副教授,研究方向为场地特征污染物的筛查、识别与健康风险评估,E-mail:yangyan1209@gdut.edu.cn
  • 1. 广东工业大学环境科学与工程学院, 环境健康与污染控制研究院, 粤港澳污染物暴露与健康联合实验室, 广东省环境催化与健康风险控制重点实验室, 广州 510006;
  • 2. 化学与精细化工广东省实验室, 汕头 515041;
  • 3. 广州大学环境科学与工程学院, 珠江三角洲水质安全与保护教育部重点实验室, 广东省放射性核素污染控制与资源化重点实验室, 广州 510006
基金项目:

国家自然科学基金资助项目(41907299,42077321);国家重点研发计划(2018YFC1801102);化学与精细化工广东省实验室科研启动项目(2032008)

摘要: 壬基酚(NPs)是一类典型的环境内分泌干扰物,具有较强的亲脂性,在土壤及沉积物等环境介质中难降解,并在生物体内具有蓄积性和高毒性,被列入我国“十四五”新污染物管控名单。NPs理论上存在211种同分异构体,而工业品NPs则是由50~80种同分异构体组成的混合物。已有充分证据显示NPs的环境行为及毒性效应呈异构体特异性差异,因此,必须从异构体分子水平上厘清NPs的环境行为、人体暴露及潜在毒性效应等,从而更精准地评估及预测其生态与健康风险。本文归纳了近些年国内外学者针对NPs同分异构体理化性质、工业品组成特征、环境行为及潜在的毒性效应等方面的研究进展,并对当前研究的瓶颈进行了梳理,展望了今后的主要研究方向。

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