环境中的氧化多环芳烃综述

张玉洁, 云洋. 环境中的氧化多环芳烃综述[J]. 环境化学, 2021, (1): 150-163. doi: 10.7524/j.issn.0254-6108.2020022802
引用本文: 张玉洁, 云洋. 环境中的氧化多环芳烃综述[J]. 环境化学, 2021, (1): 150-163. doi: 10.7524/j.issn.0254-6108.2020022802
ZHANG Yujie, YUN Yang. Oxygenated polycyclic aromatic hydrocarbons in the environment: A review[J]. Environmental Chemistry, 2021, (1): 150-163. doi: 10.7524/j.issn.0254-6108.2020022802
Citation: ZHANG Yujie, YUN Yang. Oxygenated polycyclic aromatic hydrocarbons in the environment: A review[J]. Environmental Chemistry, 2021, (1): 150-163. doi: 10.7524/j.issn.0254-6108.2020022802

环境中的氧化多环芳烃综述

    通讯作者: 云洋, E-mail: yunyang@sxu.cn
  • 基金项目:

    国家自然科学基金(21677091,21477070,91543203)和山西省奖学金委员会(2015-006)资助.

Oxygenated polycyclic aromatic hydrocarbons in the environment: A review

    Corresponding author: YUN Yang, yunyang@sxu.cn
  • Fund Project: Supported by the National Science Foundation of China (21677091, 21477070, 91543203) and Shanxi Scholarship Council of China (2015-006).
  • 摘要: 氧化多环芳烃(OPAHs)是芳环上具有至少一个羰基氧(CO)的PAH衍生物,广泛存在于环境中.氧化多环芳烃主要通过含碳燃料的燃烧和PAHs的转化释放到环境中,且其较稳定难降解,因此OPAHs被称为生物和化学降解的"末端产物".目前,在多种动物组织样本中都可检测出OPAHs,并发现OPAHs可能比亲代PAHs具有更强的毒性.本文阐述了OPAHs的理化性质、来源、测定方法、环境分布、转运和转化、(生态)毒理学效应及其毒性作用机制,并对今后的研究方向进行了展望,进而为该类化合物的环境污染及生态风险评估提供相应参考.
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  • [1] LUNDSTEDT S, WHITE P A, LEMIEUX C L, et al. Sources, fate, and toxic hazards of oxygenated polycyclic aromatic hydrocarbons (PAHs) at PAH-contaminated sites[J]. Ambio, 2007, 36(6):475-485.
    [2] PARNIS J M, MACKAY D, HARNER T. Temperature dependence of Henry's law constants and KOA for simple and heteroatom-substituted PAHs by COSMO-RS[J]. Atmospheric Environment, 2015, 110:27-35.
    [3] UMBUZEIRO G A, FRANCO A, MARTINS M H, et al. Mutagenicity and DNA adduct formation of PAH, nitro-PAH, and oxy-PAH fractions of atmospheric particulate matter from Sao Paulo, Brazil[J]. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2008, 652(1):72-80.
    [4] WANG W, JARIYASOPIT N, SCHRLAU J, et al. Concentration and photochemistry of PAHs, NPAHs, and OPAHs and toxicity of PM2.5 during the Beijing Olympic Games[J]. Environmental Science & Technology, 2011, 45(16):6887-6895.
    [5] SHEN G, TAO S, WANG W, et al. Emission of oxygenated polycyclic aromatic hydrocarbons from indoor solid fuel combustion[J]. Environmental Science & Technology, 2011, 45(8):3459-3465.
    [6] SOUZA K F, CARVALHO L R F, ALLEN A G, et al. Diurnal and nocturnal measurements of PAH, nitro-PAH, and oxy-PAH compounds in atmospheric particulate matter of a sugar cane burning region[J]. Atmospheric Environment, 2014, 83:193-201.
    [7] LI X, ZHENG Y, GUAN C, et al. Effect of biodiesel on PAH, OPAH, and NPAH emissions from a direct injection diesel engine[J]. Environmental Science and Pollution Research, 2018, 25:34131-34138.
    [8] JAKOBER C A, RIDDLE S G, ROBERT M A, et al. Quinone emissions from gasoline and diesel motor vehicles[J]. Environmental Science & Technology, 2007, 41(13):4548-4554.
    [9] KARAVALAKIS G, BOUTSIKA V, STOURNAS S, et al. Biodiesel emissions profile in modern diesel vehicles. Part 2:Effect of biodiesel origin on carbonyl, PAH, nitro-PAH and oxy-PAH emissions[J]. Science of the total Environment, 2011, 409(4):738-747.
    [10] WEI S, HUANG B, LIU M, et al. Characterization of PM2.5-bound nitrated and oxygenated PAHs in two industrial sites of South China[J]. Atmospheric Research, 2012, 109:76-83.
    [11] SHEN H, HUANG Y, WANG R, et al. Global atmospheric emissions of polycyclic aromatic hydrocarbons from 1960 to 2008 and future predictions[J]. Environmental Science & Technology, 2013, 47(12):6415-6424.
    [12] AKIMOTO Y, AOKI T, NITO S, et al. Oxygenated polycyclic aromatic hydrocarbons from MSW incinerator fly ash[J]. Chemosphere, 1997, 34(2):263-273.
    [13] CHIBWE L, GEIER M C, NAKAMURA J, et al. Aerobic bioremediation of PAH contaminated soil results in increased genotoxicity and developmental toxicity[J]. Environmental Science & Technology, 2015, 49(23):13889-13898.
    [14] 王宏亮,陈雨,夏凡.化学氧化法对多环芳烃污染土壤修复应用探讨[J].绿色科技, 2019(12):139-141. WANG H L, CHEN Y, XIA F. Discussion on application of chemical oxidation to remediation of polycyclic aromatic hydrocarbon contaminated soil[J]. Journal of Green Science and Technology, 2019

    , (12):139-141(in Chinese).

    [15] 侯梅芳, 潘栋宇, 黄赛花,等. 微生物修复土壤多环芳烃污染的研究进展[J]. 生态环境学报, 2014(7):1233-1238. HOU M F, PAN D Y, HUANG S H. Microbial remediation of polycyclic aromatic hydrocarbons contaminated soil:A review[J]. Ecology and Environment Sciences, 2014

    (7):1233-1238(in Chinese).

    [16] 范淑秀, 李培军, 何娜,等. 多环芳烃污染土壤的植物修复研究进展[J]. 农业环境科学学报, 2007, 26(6):2007-2013.

    FAN S X, LI P J, HE N, et al. Research of phytoremediation on contaminated soil with polycyclic aromatic hydrocarbons (PAHs)[J]. Journal of Agro-Environment Science, 2007, 26(6):2007-2013(in Chinese).

    [17] ANDERSSON B E, HENRYSSON T. Accumulation and degradation of dead-end metabolites during treatment of soil contaminated with polycyclic aromatic hydrocarbons with five strains of white-rot fungi[J]. Applied Microbiology and Biotechnology, 1996, 46(5/6):647-652.
    [18] OBRIST D, ZIELINSKA B, PERLINGER J A. Accumulation of polycyclic aromatic hydrocarbons (PAHs) and oxygenated PAHs (OPAHs) in organic and mineral soil horizons from four US remote forests[J]. Chemosphere, 2015, 134:98-105.
    [19] HUANG W, HUANG B, BI X, et al. Emission of PAHs, NPAHs and OPAHs from residential honeycomb coal briquette combustion[J]. Energy & Fuels, 2014, 28(1):636-642.
    [20] AZURE L E. Polycyclic Aromatic Hydrocarbons and oxygenated polycyclic aromatic hydrocarbons (PAHs and Oxy-PAHs) in house dust samples in relation to smoking behavior in the home[D]. San Diego:San Diego State University, 2016.
    [21] KEYTE I J, HARRISON R M, LAMMEL G. Chemical reactivity and long-range transport potential of polycyclic aromatic hydrocarbons-a review[J]. Chemical Society Reviews, 2013, 42(24):9333-9391.
    [22] ATKINSON R, AREY J. Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons:Formation of atmospheric mutagens[J]. Environmental Health Perspectives, 1994, 102(suppl 4):117-126.
    [23] YU H. Environmental carcinogenic polycyclic aromatic hydrocarbons:Photochemistry and phototoxicity[J]. Journal of Environmental Science and Health, Part C, 2002, 20(2):149-183.
    [24] CERNIGLIA C E. Fungal metabolism of polycyclic aromatic hydrocarbons:Past, present and future applications in bioremediation[J]. Journal of Industrial Microbiology & Biotechnology, 1997, 19(5):324-333.
    [25] BANDOWE B A M, MEUSEL H, HUANG R, et al. PM2.5-bound oxygenated PAHs, nitro-PAHs and parent-PAHs from the atmosphere of a Chinese megacity:Seasonal variation, sources and cancer risk assessment[J]. Science of the Total Environment, 2014, 473:77-87.
    [26] ALVES C A, VICENTE A M P, GOMES J, et al. Polycyclic aromatic hydrocarbons (PAHs) and their derivatives (oxygenated-PAHs, nitrated-PAHs and azaarenes) in size-fractionated particles emitted in an urban road tunnel[J]. Atmospheric Research, 2016, 180:128-137.
    [27] TOMAZ S, SHAHPOURY P, JAFFREZO J L, et al. One-year study of polycyclic aromatic compounds at an urban site in Grenoble (France):Seasonal variations, gas/particle partitioning and cancer risk estimation[J]. Science of the Total Environment, 2016, 565:1071-1083.
    [28] 姜盼. 济南春季大气细颗粒物PM2.5中多环芳烃(PAHs)及其衍生物(NPAHs,OPAHs)的污染特征和来源解析[D]. 济南:山东大学, 2018. JIANG P. Characteristics and source of PM2.5-bound PAHs, NPAHs and OPAHs in Jinan in spring[D]. Jinan:Shandong University, 2018

    (in Chinese).

    [29] 李岩岩. 济南冬季室内外大气PM2.5中多环芳烃(PAHs)及其衍生物(NPAHs,OPAHs)的污染特征和来源解析[D]. 济南:山东大学, 2018. LI Y Y. Characteristics and source of PM2.5-bound PAHs, NPAHs and OPAHs in outside of Jinan in winter[D]. Jinan:Shandong University, 2018

    (in Chinese).

    [30] NIEDERER M. Determination of polycyclic aromatic hydrocarbons and substitutes (nitro-, oxy-PAHs) in urban soil and airborne particulate by GC-MS and NCI-MS/MS[J]. Environmental Science and Pollution Research, 1998, 5(4):209-225.
    [31] WEI C, HAN Y, BANDOWE B A M, et al. Occurrence, gas/particle partitioning and carcinogenic risk of polycyclic aromatic hydrocarbons and their oxygen and nitrogen containing derivatives in Xi'an, central China[J]. Science of the Total Environment, 2015, 505:814-822.
    [32] 张俊美. 山东典型地区PM2.5中无机元素、多环芳烃及其衍生物污染特征和氧化潜势[D]. 济南:山东大学, 2019. ZHANG J M. Pollution characteristics and oxidation potential of inorganic elements, polycyclic aromatic hydrocarbons and their derivatives in PM2.5 in typical areas of Shandong[D]. Jinan:Shandong University, 2019

    (in Chinese).

    [33] CAI C Y, LI J Y, WU D, et al. Spatial distribution, emission source and health risk of parent PAHs and derivatives in surface soils from the Yangtze River Delta, eastern China[J]. Chemosphere, 2017, 178:301-308.
    [34] DSIKOWITZKY L, SCHWARZBAUER J, KRONIMUS A, et al. The anthropogenic contribution to the organic load of the Lippe River (Germany). Part I:qualitative characterisation of low-molecular weight organic compounds[J]. Chemosphere, 2004, 57(10):1275-1288.
    [35] QIAO M, QI W, LIU H, et al. Oxygenated, nitrated, methyl and parent polycyclic aromatic hydrocarbons in rivers of Haihe River System, China:Occurrence, possible formation, and source and fate in a water-shortage area[J]. Science of the Total Environment, 2014, 481:178-185.
    [36] LAYSHOCK J A, WILSON G, ANDERSON K A. Ketone and quinone-substituted polycyclic aromatic hydrocarbons in mussel tissue, sediment, urban dust, and diesel particulate matrices[J]. Environmental Toxicology and Chemistry, 2010, 29(11):2450-2460.
    [37] DASGUPTA S, CAO A, MAUER B, et al. Genotoxicity of oxy-PAHs to Japanese medaka (Oryzias latipes) embryos assessed using the comet assay[J]. Environmental Science and Pollution Research, 2014, 21(24):13867-13876.
    [38] BANDOWE B A M, WILCKE W. Analysis of polycyclic aromatic hydrocarbons and their oxygen-containing derivatives and metabolites in soils[J]. Journal of Environmental Quality, 2010, 39(4):1349-1358.
    [39] LI W, WANG C, SHEN H, et al. Concentrations and origins of nitro-polycyclic aromatic hydrocarbons and oxy-polycyclic aromatic hydrocarbons in ambient air in urban and rural areas in northern China[J]. Environmental Pollution, 2015, 197:156-164.
    [40] LUNDSTEDT S, BANDOWE B A M, WILCKE W, et al. First intercomparison study on the analysis of oxygenated polycyclic aromatic hydrocarbons (oxy-PAHs) and nitrogen heterocyclic polycyclic aromatic compounds (N-PACs) in contaminated soil[J]. TRAC Trends in Analytical Chemistry, 2014, 57:83-92.
    [41] MIRIVEL G, RIFFAULT V, GALLOO J C. Simultaneous determination by ultra-performance liquid chromatography-atmospheric pressure chemical ionization time-of-flight mass spectrometry of nitrated and oxygenated PAHs found in air and soot particles[J]. Analytical and Bioanalytical Chemistry, 2010, 397(1):243-256.
    [42] 乔梦, 齐维晓, 赵旭, 等. 多环芳烃及其衍生物在北京典型污水处理厂中的存在及去除[J]. 环境科学, 2016, 37(4):1451-1459.

    QIAO M, QI W X, ZHAO X, et al. Occurrence and removal of polycyclic aromatic hydrocarbons and their derivatives in typical wastewater treatment plants in Beijing[J]. Environmental Science, 2016, 37(4):1451-1459(in Chinese).

    [43] 曹巍, 乔梦, 张一心, 等. 典型污水处理厂对多环芳烃及其衍生物的去除及再生水健康风险研究[J]. 生态毒理学报, 2016, 11(3):173-179.

    CAO W, QIAO M, ZHANG Y X, et al. Removal of parent and substituted polycyclic aromatic hydrocarbons in typical wastewater treatment plants and health risk assessment of re-claimed water[J]. Asian Journal of Ecotoxicology, 2016, 11(3):173-179(in Chinese).

    [44] ALBINET A, NALIN F, TOMAZ S, et al. A simple QuEChERS-like extraction approach for molecular chemical characterization of organic aerosols:Application to nitrated and oxygenated PAH derivatives (NPAH and OPAH) quantified by GC-NICIMS[J]. Analytical and Bioanalytical Chemistry, 2014, 406(13):3131-3148.
    [45] COCHRAN R E, DONGARI N, JEONG H, et al. Determination of polycyclic aromatic hydrocarbons and their oxy-, nitro-, and hydroxy-oxidation products[J]. Analytica Chimica Acta, 2012, 740:93-103.
    [46] 付晓芳, 刘煜, 李伟. GC-MS测定大气中的硝基和含氧多环芳烃[C]//第二十届全国色谱学术报告会及仪器展览会, 2015. FU X F, LIU Y, LI W. Determination of nitro and oxygen-containing polycyclic aromatic hydrocarbons in the atmosphere by GC-MS[C]//Proceedings of the 20th National Chromatographic Symposium and Instrument Exhibition, 2015(in Chinese).
    [47] 魏崇, BANDOWE B A M, MEUSEL H, 等. 同时测定大气中气态和颗粒态多环芳烃及其含氧/氮衍生物的新方法[C]//十一届全国气溶胶会议暨第十届海峡两岸气溶胶技术研讨会, 2013. WEI C, BANDOWE B A M, MEUSEL H, et al. New method for simultaneous determination of gaseous and particulate polycyclic aromatic hydrocarbons and their oxygen/nitrogen derivatives in the atmosphere[C]//The 11th National Aerosol Conference cum the 10th Strait Seminar on Aerosol Technology, 2013

    (in Chinese).

    [48] RINGUET J, ALBINET A, LEOZ-GARZIANDIA E, et al. Reactivity of polycyclic aromatic compounds (PAHs, NPAHs and OPAHs) adsorbed on natural aerosol particles exposed to atmospheric oxidants[J]. Atmospheric Environment, 2012, 61:15-22.
    [49] HUANG B, LIU M, BI X, et al. Phase distribution, sources and risk assessment of PAHs, NPAHs and OPAHs in a rural site of Pearl River Delta region, China[J]. Atmospheric Pollution Research, 2014, 5(2):210-218.
    [50] 马英歌, 戴海夏, 李莉, 等. GC-MS/MS法测定PM2.5中的氧基多环芳烃含量[J]. 环境化学, 2017, 36(8):195-197.

    MA Y G, DAI H X, LI L, et al. The contents of PM2.5-bound PAHs by GC-MS/MS[J]. Environmental Chemistry, 2017,36(8):195-197(in Chinese).

    [51] 许丹丹,饶竹,梁汉东.气相色谱-质谱法同时测定地下水中36种多环芳烃及其衍生物[J]. 理化检验(化学分册), 2019, 55(1

    ):31-38. XU D D, RAO Z, LIANG H D. Simultaneous determination of 36 kinds of polycyclic aromatic hydrocarbons and their derivatives in groundwater by gas chromatography-mass spectrometry[J]. Physical Testing and Chemical Analysis Part B:Chemical Analysis, 2019, 55(1):31-38(in Chinese).

    [52] MANZANO C, HOH E, SIMONICH S L M. Quantification of complex polycyclic aromatic hydrocarbon mixtures in standard reference materials using comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry[J]. Journal of Chromatography A, 2013, 1307:172-179.
    [53] FUJIWARA F, GUIÑEZ M, CERUTTI S, et al. UHPLC-(+) APCI-MS/MS determination of oxygenated and nitrated polycyclic aromatic hydrocarbons in airborne particulate matter and tree barks collected in Buenos Aires city[J]. Microchemical Journal, 2014, 116:118-124.
    [54] GHISLAIN T, FAURE P, MICHELS R. Detection and monitoring of PAH and Oxy-PAHs by high resolution mass spectrometry:comparison of ESI, APCI and APPI source detection[J]. Journal of the American Society for Mass Spectrometry, 2012, 23(3):530-536.
    [55] TIAN M, YANG F M, CHEN S J, et al. Atmospheric deposition of polycyclic aromatic compounds and associated sources in an urban and a rural area of Chongqing, China[J]. Chemosphere, 2017, 187:78-87.
    [56] GAO Y, YANG L, CHEN J, et al. Nitro and oxy-PAHs bounded in PM2.5 and PM1.0 under different weather conditions at Mount Tai in Eastern China:Sources, long-distance transport, and cancer risk assessment[J]. Science of the Total Environment, 2018, 622:1400-1407.
    [57] ALVES C A, VICENTE A M, CUSTÓDIO D, et al. Polycyclic aromatic hydrocarbons and their derivatives (nitro-PAHs, oxygenated PAHs, and azaarenes) in PM2.5 from Southern European cities[J]. Science of the Total Environment, 2017, 595:494-504.
    [58] LEE H H, CHOI N R, LIM H B, et al. Characteristics of oxygenated PAHs in PM10 at Seoul, Korea[J]. Atmospheric Pollution Research, 2018, 9(1):112-118.
    [59] ROSARIO SIENRA M M. Oxygenated polycyclic aromatic hydrocarbons in urban air particulate matter[J]. Atmospheric Environment, 2006, 40(13):2374-2384.
    [60] RINGUET J, ALBINET A, LEOZ-GARZIANDIA E, et al. Diurnal/nocturnal concentrations and sources of particulate-bound PAHs, OPAHs and NPAHs at traffic and suburban sites in the region of Paris (France)[J]. Science of the Total Environment, 2012, 437:297-305.
    [61] ALBINET A, LEOZ-GARZIANDIA E, BUDZINSKI H, et al. Nitrated and oxygenated derivatives of polycyclic aromatic hydrocarbons in the ambient air of two French alpine valleys:Part 1:Concentrations, sources and gas/particle partitioning[J]. Atmospheric Environment, 2008, 42(1):43-54.
    [62] DELGADO-SABORIT J M, ALAM M S, POLLITT K J G, et al. Analysis of atmospheric concentrations of quinones and polycyclic aromatic hydrocarbons in vapour and particulate phases[J]. Atmospheric Environment, 2013, 77:974-982.
    [63] LAMMEL G, SEHILI A M, BOND T C, et al. Gas/particle partitioning and global distribution of polycyclic aromatic hydrocarbons:a modelling approach[J]. Chemosphere, 2009, 76(1):98-106.
    [64] LI W, SHEN G, YUAN C, et al. The gas/particle partitioning of nitro-and oxy-polycyclic aromatic hydrocarbons in the atmosphere of northern China[J]. Atmospheric Research, 2016, 172:66-73.
    [65] WEI C, BANDOWE B A M, HAN Y, et al. Polycyclic aromatic hydrocarbons (PAHs) and their derivatives (alkyl-PAHs, oxygenated-PAHs, nitrated-PAHs and azaarenes) in urban road dusts from Xi'an, Central China[J]. Chemosphere, 2015, 134:512-520.
    [66] WILCKE W, BANDOWE B A M, LUESO M G, et al. Polycyclic aromatic hydrocarbons (PAHs) and their polar derivatives (oxygenated PAHs, azaarenes) in soils along a climosequence in Argentina[J]. Science of the Total Environment, 2014, 473:317-325.
    [67] SUN Z, ZHU Y, ZHUO S, et al. Occurrence of nitro-and oxy-PAHs in agricultural soils in eastern China and excess lifetime cancer risks from human exposure through soil ingestion[J]. Environment International, 2017, 108:261-270.
    [68] BIACHE C, MANSUY-HUAULT L, FAURE P, et al. Effects of thermal desorption on the composition of two coking plant soils:Impact on solvent extractable organic compounds and metal bioavailability[J]. Environmental Pollution, 2008, 156(3):671-677.
    [69] BANDOWE B A M, BIGALKE M, KOBZA J, et al. Sources and fate of polycyclic aromatic compounds (PAHs, oxygenated PAHs and azaarenes) in forest soil profiles opposite of an aluminium plant[J]. Science of the Total Environment, 2018, 630:83-95.
    [70] MCKONE T E, MADDALENA R L. Plant uptake of organic pollutants from soil:Bioconcentration estimates based on models and experiments[J]. Environmental Toxicology and Chemistry, 2007, 26(12):2494-2504.
    [71] ODA J, NOMURA S, YASUHARA A, et al. Mobile sources of atmospheric polycyclic aromatic hydrocarbons in a roadway tunnel[J]. Atmospheric Environment, 2001, 35(28):4819-4827.
    [72] BANDOWE B A M, LUESO M G, WILCKE W. Oxygenated polycyclic aromatic hydrocarbons and azaarenes in urban soils:A comparison of a tropical city (Bangkok) with two temperate cities (Bratislava and Gothenburg)[J]. Chemosphere, 2014, 107:407-414.
    [73] BANDOWE B A M, SOBOCKA J, WILCKE W. Oxygen-containing polycyclic aromatic hydrocarbons (OPAHs) in urban soils of Bratislava, Slovakia:patterns, relation to PAHs and vertical distribution[J]. Environmental Pollution, 2011, 159(2):539-549.
    [74] TIDWELL L G, ALLAN S E, O'CONNELL S G, et al. PAH and OPAH flux during the deepwater horizon incident[J]. Environmental Science & Technology, 2016, 50(14):7489-7497.
    [75] 付璐婧, 李一兵, 乔梦, 等. 多环芳烃及其衍生物在北京纳污河流中的分布及健康风险[J]. 环境科学, 2019, 40(1):258-264.

    FU Y L, LI Y B, QIAO M, et al. Distribution and risk assessment of polycyclic arimatic hydrocarbons and their derivatives in wastewater-receiving rivers in Beijing[J]. Environmental Science, 2019, 40(1):258-264(in Chinese).

    [76] MACHALA M, CIGANEK M, BLÁHA L, et al. Aryl hydrocarbon receptor-mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments[J]. Environmental Toxicology and Chemistry, 2001, 20(12):2736-2743.
    [77] WITTER A E, NGUYEN M H. Determination of oxygen, nitrogen, and sulfur-containing polycyclic aromatic hydrocarbons (PAHs) in urban stream sediments[J]. Environmental Pollution, 2016, 209:186-196.
    [78] BRORSTRÖM-LUNDÉN E, REMBERGER M, KAJ L, HANSSON K, et al. Results from the Swedish National Screening Programme 2008:Screening of unintentionally produced organic contaminants[R]. Swedish Environmental Research Institute (IVL) report B1944. Göteborg, Sweden:IVL Swedish Environmental Research Institute Ltd, 2010.
    [79] BANDOWE B A M, BIGALKE M, BOAMAH L, et al. Polycyclic aromatic compounds (PAHs and oxygenated PAHs) and trace metals in fish species from Ghana (West Africa):Bioaccumulation and health risk assessment[J]. Environment International, 2014, 65:135-146.
    [80] BEESON W L, ABBEY D E, KNUTSEN S F. Long-term concentrations of ambient air pollutants and incident lung cancer in California adults:results from the AHSMOG study. Adventist Health Study on Smog[J]. Environmental Health Perspectives, 1998, 106(12):813.
    [81] CHUNG S W, TORIBA A, CHUNG H Y, et al. Activation of 5-lipoxygenase and NF-κB in the action of acenaphthenequinone by modulation of oxidative stress[J]. Toxicological Sciences, 2007, 101(1):152-158.
    [82] GURBANI D, BHARTI S K, KUMAR A, et al. Polycyclic aromatic hydrocarbons and their quinones modulate the metabolic profile and induce DNA damage in human alveolar and bronchiolar cells[J]. International journal of Hygiene and Environmental Health, 2013, 216(5):553-565.
    [83] BRACK W, ALTENBURGER R, KVSTER E, et al. Identification of toxic products of anthracene photomodification in simulated sunlight[J]. Environmental Toxicology and Chemistry, 2003, 22(10):2228-2237.
    [84] GOODALE B C, LA DU J, TILTON S C, et al. Ligand-specific transcriptional mechanisms underlie aryl hydrocarbon receptor-mediated developmental toxicity of oxygenated PAHs[J]. Toxicological Sciences, 2015, 147(2):397-411.
    [85] WINCENT E, JONSSON M E, BOTTAI M, et al. Aryl hydrocarbon receptor activation and developmental toxicity in zebrafish in response to soil extracts containing unsubstituted and oxygenated PAHs[J]. Environmental Science & Technology, 2015, 49(6):3869-3877.
    [86] KNECHT A L, GOODALE B C, TRUONG L, et al. Comparative developmental toxicity of environmentally relevant oxygenated PAHs[J]. Toxicology and Applied Pharmacology, 2013, 271(2):266-275.
    [87] ELIE M R, CHOI J, NKRUMAH-ELIE Y M, et al. Metabolomic analysis to define and compare the effects of PAHs and oxygenated PAHs in developing zebrafish[J]. Environmental Research, 2015, 140:502-510.
    [88] YUN Y, ZHANG Y, LI G, et al. Embryonic exposure to oxy-polycyclic aromatic hydrocarbon interfere with pancreatic β-cell development in zebrafish via altering DNA methylation and gene expression[J]. Science of the Total Environment, 2019, 660:1602-1609.
    [89] BOLTON J L, TRUSH M A, PENNING T M, et al. Role of quinones in toxicology[J]. Chemical Research in Toxicology, 2000, 13(3):135-160.
    [90] RAMDAHL T. Characterization of polar compounds such as polycyclic aromatic ketones in air pollution including wood smoke[J]. Environment International, 1985, 11(2/4):197-203.
    [91] MCCONKEY B J, DUXBURY C L, DIXON D G, et al. Toxicity of a PAH photooxidation product to the bacteria Photobacterium phosphoreum and the duckweed Lemna gibba:Effects of phenanthrene and its primary photoproduct, phenanthrenequinone[J]. Environmental Toxicology and Chemistry:An International Journal, 1997, 16(5):892-899.
    [92] PEDERSEN D U, DURANT J L, PENMAN B W, et al. Human-cell mutagens in respirable airborne particles in the northeastern United States. 1. Mutagenicity of fractionated samples[J]. Environmental Science & Technology, 2004, 38(3):682-689.
    [93] MALLAKIN A, MCCONKEY B J, MIAO G, et al. Impacts of structural photomodification on the toxicity of environmental contaminants:Anthracene photooxidation products[J]. Ecotoxicology and Environmental Safety, 1999, 43(2):204-212.
    [94] KAWANO M, UNO S, KOYAMA J, et al. Effects of oxygenated polycyclic aromatic hydrocarbons on the early life stages of Japanese Medaka[J]. Environmental Science and Pollution Research, 2017, 24(36):27670-27677.
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  • 收稿日期:  2020-02-28

环境中的氧化多环芳烃综述

    通讯作者: 云洋, E-mail: yunyang@sxu.cn
  • 山西大学环境与资源学院, 太原, 030006
基金项目:

国家自然科学基金(21677091,21477070,91543203)和山西省奖学金委员会(2015-006)资助.

摘要: 氧化多环芳烃(OPAHs)是芳环上具有至少一个羰基氧(CO)的PAH衍生物,广泛存在于环境中.氧化多环芳烃主要通过含碳燃料的燃烧和PAHs的转化释放到环境中,且其较稳定难降解,因此OPAHs被称为生物和化学降解的"末端产物".目前,在多种动物组织样本中都可检测出OPAHs,并发现OPAHs可能比亲代PAHs具有更强的毒性.本文阐述了OPAHs的理化性质、来源、测定方法、环境分布、转运和转化、(生态)毒理学效应及其毒性作用机制,并对今后的研究方向进行了展望,进而为该类化合物的环境污染及生态风险评估提供相应参考.

English Abstract

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