SUPPLEMENTARY INFORMATION. Towards streamlined identification of dioxin-like compounds in
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1 SUPPLEMENTARY INFORMATION Towards streamlined identification of dioxin-like compounds in environmental samples through integration of suspension bioassays Xiao, Hongxia # ; Brinkmann, Markus # *; Thalmann, Beat; Schiwy, Andreas; Große Brinkhaus, Sigrid; Achten, Christine; Eichbaum, Kathrin; Gembé, Carolin; Seiler, Thomas-Benjamin; Hollert, Henner * Total page number: 27, including 7 tables and 7 figures. # These authors contributed equally and share first authorship. *Corresponding authors: Prof. Dr. Henner Hollert Worringerweg Aachen, Germany Phone: +49 (0) / 26669, Fax: +49 (0) / henner.hollert@bio5.rwth-aachen.de Dr. Markus Brinkmann 44 Campus Drive Saskatoon SK S7N 5B3 Phone: (306) markus.brinkmann@usask.ca S1
2 Sampling Location Sediment sample of CNG-U were collected using a Van-Veen sampler in September 2011 at the upstream of the Yangtze River close to Chongqing. Sediment samples of HAN-C and HAN-D were collected in May 2013 at the artificial Hanfeng Lake. Figure S1: Overview map of sampling locations in the Three Gorges Reservoir area, China. The Three Gorges Reservoir covers the Yangtze River section between Jiangjin district (Chongqing) and the Three Gorges Dam. CNG-U: Upstream of Chongqing municipality, HAN-C/D: Hanfeng Lake. Detailed sampling information are available in Floehr et al. 1 S2
3 List of Standards for GC-APLI-MS Analysis For quantification of polycyclic aromatic compounds, a custom-made calibration standard and additional single compounds resulting in 73 PACs were used: naphthalene, 2- methylnaphthalene, acenaphthylene, acenaphthene, fluorene, 1-methylfluorene, phenanthrene, anthracene, 9-methylphenanthrene, 9-methylanthracene, 9,10-dimethylanthracene, fluoranthene, pyrene, 1-methylpyrene, 7H-benzo[c]fluorene, benzo[c]phenanthrene, benzo[a]anthracene, chrysene, 5-methylchrysene, cyclopenta[cd]pyrene, benzo[ghi]fluoranthene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[j]fluoranthene, dibenzo[a,e]fluoranthene, 6-methylbenzo[a]anthracene, 7,12-dimethylbenzo[a]anthracene, benzo[e]pyrene, benzo[a]pyrene, 6-methylbenzo[a]pyrene, perylene, 3-methylcholanthrene, dibenzo[a,h]anthracene, indeno[1,2,3-cd]pyrene, benzo[ghi]perylene, anthanthrene, dibenzo[a,l]anthracene, dibenzo[a,e]anthracene, dibenzo[a,i]anthracene, and dibenzo[a,h]anthracene (all custom-made PAH-mixture, Chiron, Norway), 2-methylchrysene, 4-methylchrysene, 6-methylchrysene, dibenzo[a,c]anthracene, dibenzo[a,j]anthracene, triphenylene (all single standards, Neochema, Germany), retene (single standard, Dr. Ehrenstorfer, Germany) coronene (single substance, Sigma Aldrich, Germany), 5- methylbenzo[a]anthracene, naphtho[2,3-k]fluoranthene, naphtho[2,3-b]fluoranthene, naphtho[2,3-j]fluoranthene, naphtho[1,2-k]fluoranthene, naphtho[1,2-b]fluoranthene, naphtho[2,3-e]pyrene, naphtho[2,3-a]pyrene (all single standards, Chiron, Norway), benzo[b]naphtho[1,2-d]thiophene, 4-methyldibenzo[bd]thiophene, naphtho[2,3-b]thiophene, 2,3-dimehtyldibenzo[bd]thiophene, 1-methylphenanthrene, 1,8-dimethylnaphthalene, 2,6-dimethylnaphthlene (all single standards, kindly provided by Prof. Jan T. Andersson from University of Münster), carbazole, 2-methylbenzofuran, acridine, benzo[b]furan, benzothiophene, quinoline, dibenzofuran, dibenzothiophene, indole, 2-methylquinoline (all PAH-Mix 229, Dr. Ehrenstorfer, Germany). S3
4 Fractionation Method Table S1: List of single compounds used for establishing the relationship between log K ow and retention time (RT). Octanol-water partitioning coefficients (log K ow ) were obtained using US-EPA EPI Suite. Experimental data were preferred over predicted values. No. Comp. CAS No. Supplier (purity) MW (g mol -1 ) log K ow (-) RT (min) 1 Quinoline abcr chemicals, Karlsruhe, Germany (>98%) Indole abcr chemicals, Karlsruhe, Germany (>99%) Methylquinoline abcr chemicals, Karlsruhe, Germany (>98%) Benzofuran Sigma-Aldrich, Steinheim, Germany (>99%) Benzothiophene abcr chemicals, Karlsruhe, Germany (>98%) Methylbenzofuran Sigma-Aldrich, Steinheim, Germany ( 96%) Carbazole abcr chemicals, Karlsruhe, Germany (~95%) Naphthalene LGC Standards, Wesel, Germany (analytical standard) Acridine Merck, Darmstadt, Germany (>98%)S ,3-Dimethylbenzofuran Sigma-Aldrich, Steinheim, Germany ( 97%) Acenaphthene LGC Standards, Wesel, Germany(analytical standard) Acenaphthylene LGC Standards, Wesel, Germany (analytical standard) Biphenyl LGC Standards, Wesel, Germany (analytical standard) Dibenzofuran Sigma-Aldrich, Steinheim, Germany (~98%) Fluorene LGC Standards, Wesel, Germany (analytical standard) Xanthene Sigma-Aldrich, Steinheim, Germany (>99%) S4
5 17 Dibenzothiophene abcr chemicals, Karlsruhe, Germany (>98%) Anthracene LGC Standards, Wesel, Germany (analytical standard) Phenanthrene LGC Standards, Wesel, Germany (analytical standard) β-naphthoflavone Sigma-Aldrich, Steinheim, Germany ( 98%) Pyrene LGC Standards, Wesel, Germany(analytical standard) Fluoranthene LGC Standards, Wesel, Germany (analytical standard) Hexachlorobenzene Sigma-Aldrich, Steinheim, Germany (analytical standard) Benzo[a]anthracene LGC Standards, Wesel, Germany (analytical standard) Benzo[b]fluoranthene LGC Standards, Wesel, Germany (analytical standard) Chrysene LGC Standards, Wesel, Germany (analytical standard) Benzo[a]pyrene LGC Standards, Wesel, Germany (analytical standard) Benzo[k]fluoranthene LGC Standards, Wesel, Germany (analytical standard) Benzo[ghi]perylene LGC Standards, Wesel, Germany (analytical standard) Dibenzo[a,h]anthracene LGC Standards, Wesel, Germany (analytical standard) Indeno[1,2,3-cd]pyrene LGC Standards, Wesel, Germany (analytical standard) ,3,7,8-TCDD Sigma-Aldrich, Steinheim, Germany (analytical standard) PCB Dr. Ehrenstorfer, Augsburg, Germany (analytical standard) S5
6 Development and Validation of the Fractionation Method Figure S2: Linear regression of chromatographic retention time versus the n-octanol/water partitioning coefficient (log K ow ) for a total number of 33 chemicals. The straight line is the regression line; the shaded area indicates the 95 % prediction band. S6
7 Fractionation of Environmental Samples Table S2: Concentrations of the 16 EPA-PAHs in sediment samples from the Yangtze River, China; CNG-U, HAN-C, HAN-D (Figures S5 and S6). Limit of detection (LOD): 10 µg kg -1. From Floehr et al. 1 Concentration (µg kg -1 ) Compound CNG-U HAN-D HAN-C Naphthalene Acenaphthylene Acenaphthene 33 n.d. n.d. Fluorene Phenanthrene Anthracene Fluoranthene Pyrene Benzo[a]anthracene Chrysene Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo[a]pyrene 76 n.d. n.d. Indeno[1,2,3-cd]pyrene 57 n.d. n.d. Dibenzo[a,h]anthracene 12 n.d. n.d. Benzo[ghi]perylene Σ 16 EPA-PAHs 1, n.d.: below detection limits S7
8 Table S3: Characteristics and concentrations of 17 PCDD/Fs and 12 dl-pcbs in sediments from EBR and ZE. Modified from Eichbaum at al Ehrenbreitstein harbor Zollelbe Acronym EBR ZE River system Unit km Rhine main stream Elbe cut-off meander 0.1 Longitude Latitude Sampling date Grab (Max. sampling depth) Van-Veen grab (15 cm) Van-Veen grab (15 cm) TOC (g kg -1 ) Loss on ignition (%) 10.6 ± ± 0.3 Concentration of 12 dl-pcb 4.38 ng g -1 dw 9.72 ng g -1 dw Concentration of 17 PCDD/F 1.06 ng g -1 dw 3.70 ng g -1 dw Micro-EROD EC25 TEQ of PCB fraction (pg g -1 dw) 16.7 ± ± 18.8 Micro-EROD EC25 TEQ of PCDD/F fraction (pg g -1 dw) 63.7 ± ± 32.1 S8
9 Recovery of Analytes During Fractionation Table S4: Recovery of the 16 EPA-PAHs after fractionation of 10 µl of a 625 µg L -1 standard solution was determined by means of GC-MS in three replicates. No. Compound Mean recovery (%) Standard deviation (%) 1 Naphthalene Acenaphthylene Acenaphthene Fluorene Phenanthrene Anthracene Fluoranthene Pyrene Benzo[a]anthracene Chrysene Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo[a]pyrene Indeno[1,2,3-cd]pyrene Dibenzo[a,h]anthracene Benzo[ghi]perylene S9
10 Fractionation of Environmental Samples Figure S3: Micro-EROD results of HPLC-fractionated sediment extract HAN-D (Yangtze River, China); 10 µl of a 1 g SEQ ml -1 extract were fractionated. Asterisks denote significant differences between fractions and control (one-way ANOVA with Holm-Sidak s post-hoc test, p 0.05). Shaded areas indicate the typical retention time ranges of the substance classes screened as single substances. Figure S4: Micro-EROD results of HPLC-fractionated sediment extract HAN-C (Yangtze River, China); 10 µl of a 1 g SEQ ml -1 extract were fractionated. Asterisks denote significant differences between fractions and control (one-way ANOVA with Holm-Sidak s post-hoc test, p 0.05). Shaded areas indicate the typical retention time ranges of the substance classes screened as single substances. S10
11 Table S5 Concentrations of various polycyclic aromatic compounds (PACs) in fractions F1 to F5 of an extract of sediment sample CNG-U, Yangtze River, China. Concentration (µg kg -1 ) Compound F1 F2 F3 F4 F5 Naphthalene n.d. n.d. n.d. n.d. n.d. 2-Methylnaphthalene n.d. n.d. n.d. n.d. n.d. 1,8-Dimethylnaphthalene n.d. n.d. n.d. n.d. n.d. 2,6-Dimethylnaphthalene n.d. n.d. n.d. n.d. n.d. Acenaphthene n.d. n.d. n.d. n.d. n.d. Fluorene n.d n.d. 1-Methylfluorene n.d. n.d. n.d. n.d. n.d. Phenanthrene n.d. n.d. 9-Methylphenanthrene Methylphenanthrene Retene Anthracene n.d n.d. n.d. n.d. 9-Methylanthracene n.d. n.d. n.d. n.d. n.d. 9,10-Dimethylanthracene n.d. n.d. n.d. n.d. n.d. Fluoranthene n.d n.d n.d. Pyrene n.d n.d. n.d. n.d. 1-Methylpyrene H-Benzo[c]fluorene Benzo[ghi]fluoranthene n.d. n.d. n.d. Benzo[c]phenanthrene n.d. n.d. Benzo[a]anthracene n.d. n.d. n.d. 5-Methylbenzo[a]anthracene n.d. 6-Methylbenzo[a]anthracene n.d ,12-Dimethylbenzo[a]anthracene Chrysene n.d. n.d. n.d. Triphenylene S11
12 2-Methylchrysene n.d n.d. n.d. n.d. 4-Methylchrysene n.d n.d. n.d. 6-Methylchrysene n.d. 5-Methylchrysene n.d Benzo[b]fluoranthene n.d Benzo[k]fluoranthene n.d n.d. n.d. n.d. Benzo[a]pyrene n.d n.d. 6-Methylbenzo[a]pyrene n.d n.d. n.d. Benzo[e]pyrene Perylene n.d n.d. 3-Methylcholanthrene n.d. n.d. n.d. n.d. n.d. Indeno[1,2,3-cd]-pyrene n.d. n.d n.d. Dibenzo[a,h]anthracene n.d n.d. n.d. n.d. Dibenzo[a,c]anthracene Dibenzo[a,j]anthracene Anthanthrene Benzo[ghi]perylene n.d. n.d n.d. Coronene n.d. n.d. n.d. n.d Naphtho[1,2-b]-fluoranthene + Naphtho[2,3-a]-pyrene Naphtho[2,3-j]-fluoranthene + Naphtho[1,2-k]-fluoranthene n.d Naphtho[2,3-b]-fluoranthene n.d Naphtho[2,3-e]-pyrene n.d Naphtho[2,3-k]-fluoranthene Dibenzo[a,e]fluoranthene 0.03 n.d. n.d n.d. Dibenzo[a,e]pyrene n.d n.d Dibenzo[a,h]pyrene 0.05 n.d n.d Dibenzo[a,i]pyrene n.d. n.d. n.d Dibenzo[a,l]pyrene n.d. n.d. n.d n.d. n.d.: not detectable S12
13 Solvent control Fraction F2 S13
14 Fraction F4 Figure S5: A solvent control, as well as the factions F2 and F4 of extract of CNG-U sediment were analyzed by means of gas chromatographyatmospheric pressure laser ionization-time-of-flight-mass spectrometry (GC-APLI-MS). Labelled peaks are listed in Tables S6 and S7. Peaks present in the solvent control were excluded from further analysis. S14
15 Table S6: Detected and confirmed (bold) PACs in fraction F2 of extracts of CNG-U sediment as detected by means of gas chromatographyatmospheric pressure laser ionization-time-of-flight-mass spectrometry (GC-APLI-MS). Peak numbers refer to the peaks labeled in Figure S5. No. RT (min) Max. m/z Compound (possible) sum formula Area Intensity (cps) S/N ratio C3-Phenanthrene/Anthracene C 17 H C4- Phenanthrene/Anthracene C 18 H C5- Phenanthrene/Anthracene C 19 H C 18 H C2-Pyrene/Fluoranthene C 18 H C2-Pyrene/Fluoranthene C 18 H C 18 H 14 O C2-Pyrene/Fluoranthene C 18 H C2-Pyrene/Fluoranthene C 18 H C2-Pyrene/Fluoranthene C 18 H C4- Phenanthrene/Anthracene C 18 H C2-Pyrene/Fluoranthene C 18 H C2-Pyrene/Fluoranthene C 18 H C4-Phenanthrene/Anthracene, one double bond C 18 H C4-Phenanthrene/Anthracene, one double bond C 19 H C2-Pyrene/Fluoranthene C 18 H C3-Pyrene/Fluoranthene C 19 H C3-Pyrene/Fluoranthene C 19 H C3-Pyrene/Fluoranthene C 19 H S15
16 C3-Pyrene/Fluoranthene C 19 H Benzo[a]anthracene Chrysene C5-Phenanthrene/Anthracene, one double bond C 19 H Chrysene isomers (hypothetic) Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene Methylchrysene/Methylbenzo[a]anthracene C2-226 PAH C 20 H C1-226 PAH C 19 H Methylchrysene/Methylbenzo[a]anthracene C2-226 PAH C 20 H C1-226 PAH C 19 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-226 PAH C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H S16
17 C2-Chrysen/Benzo[a]anthracene C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C3-226 PAH C 21 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-226 PAH C 20 H C2-226 PAH C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C2-Chrysen/Benzo[a]anthracene C 20 H C3-226 PAH C 21 H Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo[e]pyrene Benzo[a]pyrene Perylen C1-228 PAH C 21 H C1-228 PAH C 21 H C1-228 PAH C 21 H S17
18 Dibenzoanthracene Dibenzoanthracene Dibenzoanthracene Dibenzoanthracene Dibenzoanthracene Table S7: Detected and confirmed (bold) PACs in fraction F4 of extracts of CNG-U sediment as detected by means of gas chromatographyatmospheric pressure laser ionization-time-of-flight-mass spectrometry (GC-APLI-MS). Peak numbers refer to the peaks labeled in Figure S5. No. RT (min) Max. m/z Compound (possible) sum formula Area Intensity (cps) S/N ratio C 9 H 18 NO C1-Phenanthrene/Anthracene C 15 H C2-Phenanthrene/Anthracene C 16 H C2-Phenanthrene/Anthracene C 16 H C6-Phenanthrene/Anthracene C 20 H C6-Phenanthrene/Anthracene C 20 H C6-Phenanthrene/Anthracene C 20 H C 8 H 5 O C6-Phenanthrene/Anthracene C 20 H C6-Phenanthrene/Anthracene C 20 H S18
19 C7-Phenanthrene/Anthracene C 21 H C 19 H 16 O C6-Phenanthrene/Anthracene C 20 H C 19 H C 12 H 7 C l2 N C 19 H 16 O C 20 H C 19 H 16 O C 18 H C 19 H 16 O C6-Phenanthrene/Anthracene, one double bond C 20 H C 21 H C 19 H 16 O C 18 H C6-Phenanthrene/Anthracene, one double bond C 20 H Benzo[a]anthracene-D C6-Phenanthrene/Anthracene, one double bond C 20 H S19
20 C6-Phenanthrene/Anthracene, one double bond C 20 H Chrysene D Chrysene C6-Phenanthrene/Anthracene, one double bond C 20 H C6-Phenanthrene/Anthracene, one double bond C 20 H C7-Phenanthrene/Anthracene, one double bond C 21 H C7-Phenanthrene/Anthracene, one double bond C 21 H C6-Phenanthrene/Anthracene, one double bond C 20 H C5-Fluoranthene/Pyrene C 21 H C6-Phenanthrene/Anthracene, one double bond C 20 H C7-Phenanthrene/Anthracene, one double bond C 21 H C7-Phenanthrene/Anthracene, one double bond C 21 H C4-Fluoranthene/Pyrene C 20 H C6-Phenanthrene/Anthracene, one double bond C 20 H C4-Fluoranthene/Pyrene C 20 H S20
21 C4-Fluoranthene/Pyrene C 20 H C4-Fluoranthene/Pyrene C 20 H C4-Fluoranthene/Pyrene C 20 H C7-Phenanthrene/Anthracene C 21 H C4-Fluoranthene/Pyrene C 20 H C6-Phenanthrene/Anthracene, one double bond C 20 H C6-Phenanthrene/Anthracene, one double bond C 20 H C4-Fluoranthene/Pyrene C 20 H C5-Fluoranthene/Pyrene C 21 H C7-Phenanthrene/Anthracene, one double bond C 21 H C4-Fluoranthene/Pyrene C 20 H C7-Phenanthrene/Anthracene, one double bond C 21 H S21
22 C6-Phenanthrene/Anthracene, one double bond C 20 H C7-Phenanthrene/Anthracene, one double bond C 21 H C5-Fluoranthene/Pyrene C 21 H C4-Fluoranthene/Pyrene C 20 H C4-Fluoranthene/Pyrene C 20 H C7-Phenanthrene/Anthracene, one double bond C21H C6-Phenanthrene/Anthracene, one double bond C 20 H C4-Fluoranthene/Pyrene C 20 H C4-Fluoranthene/Pyrene C 20 H C4-Fluoranthene/Pyrene C 20 H C5-Fluoranthene/Pyrene C 21 H C 19 H 16 S C2-228 PAH C 20 H C 19 H 16 S C5-Fluoranthene/Pyrene C 21 H C2-228 PAH C 20 H C2-228 PAH C 20 H C5-Fluoranthene/Pyrene C 21 H C3-228 PAH C 21 H C2-228 PAH C 20 H C3-228 PAH C 21 H S22
23 C3-228 PAH C 21 H C3-228 PAH C 21 H C 21 H 14 O C3-228 PAH C 21 H C 21 H 14 O C2-252 PAH C 22 H C1-252 PAH C 21 H C4-228 PAH C 22 H C2-252 PAH C 22 H C2-252 PAH C 22 H C2-252 PAH C 22 H C2-252 PAH C 22 H C 20 H 12 S C2-252 PAH C 22 H C2-252 PAH C 22 H C4-228 PAH C 22 H C2-252 PAH C 22 H C2-252 PAH C 22 H Dibenzoanthracene C 22 H C 24 H S23
24 C2-252 PAH C 22 H C3-252 PAH C 23 H C 22 H 12 O Benzo[g,h,i]perylene C 22 H 12 O C 22 H C1-Dibenzoanthracene C 23 H C1-Dibenzoanthracene C 23 H C1-Dibenzoanthracene C 23 H C1-Dibenzoanthracene C 23 H C1-Benzo[ghi]perylene C 23 H C2-Benzo[ghi]perylene C 24 H C2-Dibenzoanthracene C 24 H C2-Dibenzoanthracene C 24 H C2-Benzo[ghi]perylene C 24 H Dibenzopyrene Dibenzopyrene Dibenzopyrene Dibenzopyrene Dibenzopyrene Dibenzopyrene S24
25 C1-Dibenzopyrene C 25 H Hexacene isomers C 26 H Hexacene isomers C 26 H Hexacene isomers C 26 H S25
26 Figure S6: Micro-EROD results of HPLC-fractionated multilayer silica column-treated sediment extract (Ehrenbreitstein. Rhine. Germany); 10 µl of a 1 g SEQ ml -1 extract were fractionated. No significant differences between fractions and control were found (one-way ANOVA with Holm-Sidak s post-hoc test. p > 0.05). Shaded areas indicate typical retention time ranges of the indicated substance classes. Figure S7: Micro-EROD results of HPLC-fractionated multilayer silica column-treated sediment extract (Zollelbe. Elbe. Germany); 10 µl of a 1 g SEQ ml -1 extract were fractionated. Asterisks denote significant differences between fractions and control (one-way ANOVA with Holm-Sidak s post-hoc test. p 0.05). Shaded areas indicate typical retention time ranges of the indicated substance classes. S26
27 References 1. Floehr, T.; Scholz-Starke, B.; Xiao, H.; Koch, J.; Wu, L.; Hou, J.; Wolf, A.; Bergmann, A.; Bluhm, K.; Yuan, X.; Roß-Nickoll, M.; Schäffer, A.; Hollert, H., Yangtze Three Gorges Reservoir, China: A holistic assessment of organic pollution, mutagenic effects of sediments and genotoxic impacts on fish. Journal of Environmental Sciences 2015, 38, Eichbaum, K.; Brinkmann, M.; Nuesser, L.; Buchinger, S.; Reifferscheid, G.; Codling, G.; Jones, P.; Giesy, J. P.; Hecker, M.; Hollert, H., Bioanalytical and instrumental screening of the uptake of sediment-borne, dioxin-like compounds in roach (Rutilus rutilus). Environmental Science and Pollution Research 2016, S27
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