Metabolism and Transformation of Brominated Flame Retardants Existing in Environment and Human Body

21 6 2009 6 PROGRESS IN CHEMISTRY Vol. 21 No. 6 Jun., 2009 3 1 1,2 3 3 1 3 1,2 1,2 (11 200244 ; 21 510640 ; 31 200444), : A, ( ) ( ), A : TQ314124 + 8 ; X503 : A : 10052281X(2009) 0621364209 Metabolism and Transformation of Brominated Flame Retardants Existing in Environment and Human Body Zhang Fan 1 Yu Yingxin 1,2 3 3 Zhang Dongping 1 Wu Minghong 3 Sheng Guoying 1,2 Fu Jiamo 1,2 (11Institute of Environmental Pollution and Health, School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200244, China ; 21State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640, China ; 31Institute of Applied Radiation, School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, China) Abstract Brominated flame retardants (BFRs) are of great concern due to their wide use and adverse effects to environment and human. The existence for polybrominated diphenyl ethers ( PBDEs ), hexabromocyclododecanes (HBCDs), and tetrabromobisphenol A(TBBPA), three major kinds of BFRs found in environment and ecosystems and in human body are reviewed briefly. The degradation and biotransformation of them in environmental medium (wastewater, sludge and sediment), organism ( microorganism and animals) and human body are focused. The degradation and biotransformation of them under light and heat are of great concern also. The degradation pathway and metabolites of BFRs are introduced in detail. In addition, the future research and prospects are also discussed. Key words BFRs ; PBDEs ; HBCDs ; TBBPA ; metabolism and transformation Contents 1 Introduction 2 Existing in the environment 211 PBDEs 212 HBCDs 213 TBBPA 3 Metabolism and transformation : 2008 6, : 2008 7 3 (No. 2008CB418205) (No. 20807026) (No. OGL2200704) (No. S30109) 3 3 e2mail :yuyingxin @staff. shu. edu. cn

6 1365 311 PBDEs 312 HBCDs 313 TBBPA 4 Prospects 1 ( brominated flame retardants,bfrs),, 30 BFRs, BFRs,, BFRs, : ( polybrominated diphenylethers, PBDEs ) ( hexabromocyclododecanes, HBCDs ) A (tetrabromobisphenol A,TBBPA), (persistent organic pollutants, POPs),,,, [9 ] 2002, de Wit [1 ],, [2 ] [3 ] PBDEs, [4 ] TBBPA BFRs :PBDEs PBDEs PBDEs HBCDs TBBPA, 2 211 PBDEs PBDEs,,PBDEs,, BFRs 1979, de Carlo [5 ] PBDEs, Andersson [6 ] PBDEs, PBDEs, PBDEs 5,, [3,7 9 ] PBDEs, BFRs Gauthier [10 ] 20 PBDEs :, BDE47 99 100 2000, PBDEs, [11 ] [12 ], Zheng [13 ] PBDEs 0115 13103ng g - 1 ( ) ; [14 PBDEs 17 ] Xian [12 ] PBDEs 120ng g - 1 ( ),, [9,18 ], PBDEs 0115 3218ng g - 1 ( ) 5132 72176ng g - 1 ( ) [19,20 ], PBDEs, PBDEs > > [21 ] Wang [23 ] PBDEs, PBDEs BDE47 153, BDE209, PBDEs PBDEs, PBDEs [22 ],, PBDEs, ( ) PBDEs,BDE47 153,, ; BDEs BDEs, BDEs BDEs ;, BDE209,, Sundaryanto [24 ] PBDEs

1366 21, (612ng g - 1 ) [25 ] PBDEs 115 12ng g - 1 116 17ng g - 1, Wang [23 ] PBDEs (15124ng g - 1 ) PBDEs, [25 ],, PBDEs, ( ) PBDEs,, PBDEs 37 % [26 ], 60 % 80 % [27,28 ] Huwe [29 ],, ( ) PBDEs 69 % 100 % 212 HBCDs HBCDs 12,, 6, ( )2 2HBCD, ( )2 2HBCD, ( )2 2HBCD, 2HBCD [30 ] HBCDs,, PBDEs, HBCDs PBDEs POPs, [30 ] PBDEs, HBCDs Sellstrgm [31 ] Viscan HBCDs, HBCDs,,, 9 600 19 200ng g - 1 ( ) [32 ] HBCDs,, HBCDs [33 ],Xian [12 ] HBCDs 12 330ng g - 1 ( ), 0110 119ng g - 1 ( ) 310 78ng g - 1 ( ), Covaci [32 ] (26 10, 275ng g - 1 ), HBCDs 44ng g - 1 ( ), 312ng g - 1, HBCDs, [33 ],Yu [34 ] HBCDs (0169 3109) pg m - 3, (016 415) pg m - 3, (2 280) pg m - 3 [32,35 ] 213 TBBPA TBBPA,,, BFRs, BFRs [36 50 % 38 ], TBBPA,2002 2004 20 % [39 ],TBBPA [4 ] TBBPA ph < 710 1mg g - 1,,, ph,tbbpa, [39 ], TBBPA 34 270ng g - 1 ( ) [40,41 ],, 9175ng g - 1 ( ) [42 ], 012 2014ng L - 1 [39 ], TBBPA 717 30ng L - 1 [43 ] ; [39 ] TBBPA, 0 1191ng L - 1,Ashizuka [44 ] TBBPA 0101 0111ng g - 1 ( ), Frederiksen [45 ], Fernandes [46 ] Johnson2Restrepo [47 ] TBBPA, 3516ng g - 1 ( ) 915 012ng g - 1 ( ),,,Thomsen [48,49 ] TBBPA, 1985 1999, 4 0171ng g - 1 ( ) ; Cariou [50 ] TBBPA 310ng g - 1 7 000ng g - 1 ( ) Johnson2Restrepo [47 ] TBBPA

6 1367 TBBPA 010189ng g - 1 ( ), 010739ng g - 1 ( ), (011040ng g - 1 ) TBBPA 3 311 PBDEs 31111, Gerecke [51 ] BFRs, BDE209 HBCDs TBBPA, BDE209 1 10-3 d - 1, TBBPA ( )2 2HBCD ( )2 2HBCD > ( )2 2HBCD > > BDE209 Tokarz [8 ] BDE209,, BDE209 18s, 60d,24h 4 BDE209, ( BDE99 [57 ] OH2PBDEs MeO2 BDE119) (BDE47 BDE66), 4, PBDEs, BDE99 BDE47 66 49, BDE47 BDE17 La Guardia [52 ] BDE209,,, Haglund [53 ] PBDEs (MeO2PBDEs), PBDEs,, PBDEs, Gerecke [54 ] BDE209, BDE209 BDE206 207 208,, He [55 ] ( Sulf urospirillum multivorans) BDE209, ( Dehalococcoides species) Robbrock [7 ] 7 PBDEs(BDE196 203 197 183 153 99 47),,, Gerecke [54 ] Zhou [56 ] BDE209, BDE209, 80, ; 2,, > ;,,, BDE209,,, PBDEs,,,PBDEs PBDEs (OH2PBDEs) MeO2PBDEs, [58 PBDEs 60 ],OH2PBDEs MeO2PBDEs,, [61, 64 ], (phase ) (phase ) P450 ( CYP21A 22B 24A3),,,, ; ( ),,,, [57 ] P450 (,PCBs) :, 1,22 [58 ],,, [56 ] PBDEs PCBs,,

1368 21 PBDEs, PBDEs OH2PBDEs Tomy [65 ] 13 PBDEs( 3 10) 56d, BDE85 BDE190 ( ), BDE66 77 153 154 ( ), 3 : BDE140,, ; rn [66 ] 14 C2 BDE47, 6,, (thiol2tetrabromo diphenyl ether) ;, 5, (in vitro) Stapleton [67 ] BDE99 BDE183, BDE99 BDE47,BDE183 BDE154,, BDE99,,, Benedict [68 ] (in vitro), BDE99 BDE47, P450 BDE99, (reverse thyronine,rt3) (microsomes) BDE99, (deiodinases,di) Stapleton [69 ] BDE209 60d, 7 ( ) Van den Steen [70 ] BDE209, MeO2PBDEs, OH2PBDEs, [53,57,71 ] Marsh [58 ] 9 OH2PBDEs 6 MeO2PBDEs, OH2 MeO2PBDEs 4 5, 14 OH2 MeO2 Valters [72 ] OH2PBDEs MeO2PBDEs, OH2PBDEs, OH2PBDEs, PBDEs [73 75 ] (in vivo),, BDE209, BDEs (MeO2OH2BDEs), MeO2 2O2 Malmbrg [76 ] PBDEs 6 OH2PBDEs 2 2OH2PBDEs,, 4 OH2 PBDEs, 42OH2BDE42 32OH2BDE47 4 2OH2 BDE49 62OH2BDE47 ; Marsh [77 ] BDE47 6 3, PBDEs,,,,, [78 ] Stapleton [79 ] BDE209,24h BDE209 McKinney [78 ] 90min PBDEs,, OH2 PBDEs 31112, PBDEs Athanasiadou [61 ], 11 15 6 OH2PBDEs, 4 OH2PBDEs, OH2PBDEs, OH2 PBDEs,, PBDEs 31113 PBDEs BDE209

6 1369,Bezares2Cruz [80 ] BDE209 [89 ] Davis [90 ] Eriksson [81 ] 15 PBDEs ( 4 10) (8 2Πv v), BDE209, 3 7 8 Fang [82 ] ( ) PBDEs,,,,,, PBDE2 ;, PBDEs, : >, Rayne [83 ] 4,4 2 (BDE15), Sgderstrgm [84 ] BDE209, BDE209 ( PBDFs), ( ), [80 ], Grabda [85 ] 03 ( Gaussian 03 program) (DFT),,Br, PBDEs PBDEs PBDEs,,PBDEs, : ( PBDDs) ( PBDFs) [86 ] Buser [87 ] 510 630, PBDDs PBDFs, Nose [88 ], BDE209,200,300,,, BDE209,, BDE209,, 312 HBCDs PBDEs,HBCDs, HBCDs,119d HBCDs 75 %, 21d HBCDs 92 %, [91 ] 14 C2HBCD, 3 : ( TBCDe) (DBCDi) (CDT), Sinkkonen [92 ] HBCDs,Hiebl [93 ] HBCDs Jan k [94 ] HBCDs, 2HBCD Ueno [33 ] HBCDs, 2HBCD, [42,95,96 ] Zegers [30 ], 2 2HBCD (NADPH), 2HBCD, 2HBCD,Abdallaha [97 ], HBCDs : (PBCDs) ( TBCDs), HBr HBCDs HBCDs HBr [98 ], HBCDs 313 TBBPA PBDEs,TBBPA,Han [37 ] TBBPA (quencher) ( 1 O 2 ), TBBPA Eriksson [99 ] TBBPA 3 :42 22,62 42 22,62 42(22 ) 22,62 TBBPA (180 172 ) [100 ], Barontini [101 ] TBBPA, : A, 8, 8,, A,,, 270

1370 21 A(BPA) TBBPA Ronen [102 ] 2 2, TBBPA BPA BPA,, (genus Sphingomonas,strain WH1) BPA, 42 42 Arbeli [103 ] BPA TBBPA 3, A NaCl 2 % 3 % 30 ph 7 8 TBBPA [104 ] TBBPA [41 ], Watanabe [105 ] TBBPA TBBPA,,Ravit [106 ] TBBPA : A A, BPA ; TBBPA, ( Spartina alterniflora) TBBPA ( Phragmites australis) [106 ], TBBPA, TBBPA, TBBPA, TBBPA 13h, TBBPA, [107 ] Kuester [108 ] TBBPA 72h 90 % TBBPA,, ( < 2 %), TBBPA 82min Lilienthal [38 ] TBBPA 2d Szyma ska [109 ] TBBPA 72h, A,, TBBPA,, Chignell [110 ] TBBPA, 2,62 2,62 Szyma ska [109 ] Hakk [111 ] TBBPA 3, : 2, TBBPA, Hakk [57 ] TBBPA,, TBBPA TBBPA ( deconjugation) 4 PBDEs, TBBPA, HBCDs BFRs,, PBDEs, TBBPA,, BFRs,, 2008 4 1, BDE209, ( BDE209) (RoHS ),, PBDEs, Deca2BDE HBCDs PBDEs,,, 1997 HBCDs,,,,, HBCDs [ 1 ] De Wit C1 A. Chemosphere, 2002, 46 : 583 624 [ 2 ] (Lu H X), (Zhang Q H), (Jiang GB). (Progress in Chemistry), 2005, 17 : 554 562 [ 3 ] (Wei A X), (Wang X T), ( Xu X B). (Progress in Chemistry), 2006, 18 : 1227 1233 [ 4 ] (Li Y N), ( Zhou Q X). ( Chinese Journal of Ecology), 2008, 27 : 263 268 [ 5 ] De Carlo V J, Ann N Y. Acad. Sci., 1979, 320 : 678 681 [ 6 ] Andersson ;, Blomkvist G. Chemosphere, 1981, 10 : 1051 1060

6 1371 [ 7 ] Robbrock K R, Koryt r P, Alvarez2Cohen L. Environ. Sci. Technol., 2008, 42 : 2845 2852 [ 8 ] Tokarz J A, Ahn Mi2Y, Leng J, et al. Environ. Sci. Technol., 2008, 42 : 1157 1164 [ 9 ] Hites R A. Environ. Sci. Technol., 2004, 38 : 945 956 [10 ] Gauthier L T, Hebert C E, Weseloh D V C, et al. Environ. Sci. Technol., 2008, 42 : 1524 1530 [11 ] Shinsuke T. Marine Pollut. Bull., 2008, 57 : 267 274 [12 ] Xian Q M, Ramu K, Isobe T, et al. Chemosphere, 2008, 71 : 268 276 [13 ] Zheng GJ, Martin M, Richardson B J, et al. Marine Poll. Bull., 2004, 49 : 520 524 [14 ] Mai B X, Chen SJ, Luo XJ, et al. Environ. Sci. Technol., 2005, 39 : 3521 3527 [15 ] Chen L G, Mai B X, Bi X H, et al. Environ. Sci. Technol., 2006, 40 : 1190 1196 [16 ] Bi X H, Thomas G O, Jones K C, et al. Environ. Sci. Technol., 2007, 41 : 5647 5653 [17 ] Meng X Z, Zeng E Y, Yu L P, et al. Environ. Sci. Technol., 2007, 41 : 4882 4887 [18 ] Peng J H, Huang C W, Weng YM, et al. Chemosphere, 2007, 66 : 1990 1997 [19 ] Wan Y I, Hu J Y, Zhang K, et al. Environ. Sci. Technol., 2008, 42 : 1078 1083 [20 ] Yang F X, Zhang Q H, Xu Y, et al. Environ. Toxicol. Chem., 2008, 27 : 991 996 [21 ] Covaci A, Voorspoels S, Roosens L, et al. Chemosphere, 2008, 73 : 170 175 [22 ] Voorspoels S, Covaci A, Neels H, et al. Environ. Int., 2007, 33 : 93 97 [23 ] Wang Y W, Jiang G B, Lam P K S, et al. Environ. Int., 2007, 33 : 963 973 [24 ] Sundaryanto A, Kajiwara N, Tsydenova O, et al. Organohalog. Comp., 2005, 67 : 1315 1318 [25 ] (Qu W Y). (Doctoral Dissertation of Chinese Academy of Sciences), 2007, 5 [26 ] Harrad S, Hazrati S, Ibarra C. Environ. Sci. Technol., 2006, 40 : 4633 4638 [27 ] Jones2Otazo H A, Clarke J P, Diamond M L, et al. Environ. Sci. Technol., 2005, 39 : 5121 5130 [28 ] Tan J, Cheng S M, Loganath A, et al. Chemosphere, 2007, 66 : 985 992 [29 ] Huwe J K, Hakk H, Smith D J, et al. Environ. Sci. Technol., 2008, 42 : 2694 2700 [30 ] Zegers B N, Mets A, Bommel R V, et al. Environ. Sci. Technol., 2005, 39 : 2095 2100 [31 ] Sellstrgm U, Kierkegaard A, de Wit C, et al. Environ. Toxicol. Chem., 1998, 17 : 1065 1072 [32 ] Covaci A, Gerecke A C, Law R J, et al. Environ. Sci. Technol., 2006, 40 : 3679 3688 [33 ] Ueno D, Alaee M, Marvin C, et al. Environ. Poll., 2006, 144 : 238 247 [34 ] Yu Z Q, Peng P A, Sheng G Y, et al. J. Chromatogr. A, 2008, 1190 : 74 79 [35 ] Hoh E, Hites R A. Environ. Sci. Technol., 2005, 39 : 7794 7802 [36 ] Hornung A, Balabanovich A I, Donner S, et al. J. Anal. Appl. Pyrolysis, 2003, 70 : 723 733 [37 ] Han S K, Bilski P, Karriker B, et al. Environ. Sci. Technol., 2008, 42 : 166 172 [38 ] Lilienthal H, Verwer C M, Van der Ven L T M, et al. Toxicology, 2008, 246 : 45 54 [39 ] (Peng H). (Master Dissertation of Minzu University of China). 2007, 4 [40 ] ; berg K, Warman K, ; berg T. Chemosphere, 2002, 48 : 805 809 [41 ] Sellstrgm U, Jansson B. Chemosphere, 1995, 31 : 3085 3092 [42 ] Morris S, Allchin C R, Zegers B N, et al. Environ. Sci. Technol., 2004, 38 : 5497 5504 [43 ] Suzuki S, Hasegawa A. Anal. sci., 2006, 22 : 469 474 [44 ] Ashizuka Y, Nakagawa R, Hori T, et al. Mol. Nutr. Food Res., 2008, 52 : 273 283 [45 ] Frederiksen M, Vorkamp K, Bossi R, et al. J. Environ. Anal. Chem., 2007, 87 : 1095 1109 [46 ] Fernandes A, Dicks P, Mortimer D, et al. Mol. Nutr. Food Res., 2008, 52 : 238 249 [47 ] Johnson2Restrepo B, Adams D H, Kannan K. Chemosphere, 2008, 70 : 1935 1944 [48 ] Thomsen C, Lundanes E, Becher G. Environ. Sci. Technol., 2002, 36 : 1414 1418 [49 ] Thomsen C, Lundanes E, Becher G. J. Environ. Monit., 2001, 3 : 366 370 [50 ] Cariou R, Antignac J P, Marchand P, et al. J. Chromatogr. A, 2005, 1100 : 144 152 [51 ] Gerecke A C, Giger W, Hartmann P C, et al. Chemosphere, 2006, 64 : 311 317 [52 ] La Guardia M J, Hale R C, Harvey E. Environ. Sci. Technol., 2007, 41 : 6663 6670 [53 ] Haglund P S, Zook D R, Buser H R, et al. Environ. Sci. Technol., 1997, 31 : 3281 3287 [54 ] Gerecke A G, Hartmann P C, Heeb N V, et al. Environ. Sci. Technol., 2005, 39 : 1078 1083 [55 ] He J Z, Kristin R R, Lisa A C. Environ. Sci. Technol., 2006, 40 : 4429 4434 [56 ] Zhou J, Jiang W Y, Ding J A, et al. Chemosphere, 2007, 70 : 172 177 [57 ] Hakk H, Letcher R J. Environ. Int., 2003, 29 : 801 828 [58 ] Marsh G, Athanasiadou M, Bergman!, et al. Environ. Sci. Technol., 2004, 38 : 10 18 [59 ] Teuten E L, Xu L, Reddy C M. Science, 2005, 307 : 917 920 [60 ] Schumacher R W, Davidson B S. Didemolines A D. Tetrahedron, 1995, 51 : 10125 10130 [61 ] Athanasiadou M, Steven N, Cuadra S N, et al. Environ. Health Persp., 2008, 116 : 400 408 [62 ] Canton R F, Scholten D E A, Marsh G, et al. Toxicol. Appl.

1372 21 Pharmacol., 2008, 227 : 68 75 [63 ] He Y H, Murphy M B, Yu R M K, et al. Toxicol. Lett., 2008, 176 : 230 238 [64 ] Van Boxtel A L, Kamstra J H, Cenijn P H, et al. Environ. Sci. Technol., 2008, 42 : 1773 1779 [65 ] Tomy G T, Palace V P, Halldorson T, et al. Environ. Sci. Technol., 2004, 38 : 1496 1504 [66 ] ; rn U, Klasson2Wehler E. Xenobiotica, 1998, 28 : 199 211 [67 ] Stapleton H M, Letcher R J. Baker J E. Environ. Sci. Technol. 2004, 38, 1054 1061 [68 ] Benedict R T, Stapleton H M, Letcher R J, et al. Chemosphere, 2007, 69 : 987 993 [69 ] Stapleton H M, Alaee M, Letchwe R J, et al. Environ. Sci. Technol., 2004b, 38 : 112 119 [70 ] Van den Steen E, Covaci A, Jaspers V L B, et al. Environ. Poll., 2007, 148 : 648 653 [71 ] Asplund L, Athanasiadou M, Sjodin A, et al. Ambio, 1999, 28 : 67 76 [72 ] Valters K, Li H X, Alaee M, et al. Environ. Sci. Technol., 2005, 39 : 5612 5619 [73 ] Burreau S, Axelman J E. Toxicol. Chem., 1997, 16 : 2508 2513 [74 ] Gustafsson K, Bjgrk M E. Toxicol. Chem., 1999, 18 : 1218 1224 [75 ] Gebbink W A, Sonne C, Dietz R, et al. Environ. Pol., 2008, 152 : 621 629 [76 ] Malmbrg T, Athanasiadou M, Marsh G, et al. Environ. Sci. Technol., 2005, 39 : 5342 5348 [77 ] Marsh G, Athanasiadou M, Athanassiadis I, et al. Chemosphere, 2006, 63 : 690 697 [78 ] McKinney M A, Guise S D, Martineau D, et al. Aquat. Toxicol., 2006, 77 : 87 97 [79 ] Stapleton H M, Brazil B, Holbrook R D, et al. Environ. Sci. Technol., 2006, 40 : 4653 4658 [80 ] Bezares2Cruz J, Jafvert C T, Hua I. Environ. Sci. Technol., 2004, 38 : 4149 4156 [81 ] Eriksson J, Green K, Marsh G, et al. Environ. Sci. Technol., 2004, 38 : 3119 3125 [82 ] Fang L, Huang J, Yu G, et al. Chemosphere, 2008, 71 : 258 267 [83 ] Raynea S, Michael G, Ikonomoub M G, et al. Water Res., 2003, 37 : 551 560 [84 ] Sgderstrgm G, Sellstrgm U, de Wit C A, et al. Environ. Sci. Technol., 2004, 38 : 127 132 [85 ] Grabda M, Oleszek2Kudlak S, Shibata E, et al. J. Mol. Structure (Theochem), 2007, 822 : 38 44 [86 ] Rupp S, Metzger J W. Chemosphere, 2005, 60 : 1644 1651 [87 ] Buser H R. Environ. Sci. Technol., 1986, 20 : 404 408 [88 ] Nose K, Hashimoto S, Takahashi S, et al. Chemosphere, 2007, 68 : 120 125 [89 ] Livingstone H D, Bowen V T, Kupferman S L. J. Mar. Res., 1982, 40 : 1227 1258 [90 ] Davis J W, Gonsior S, Marty G, et al. Water Res., 2005, 39 : 1075 1084 [91 ] Davis J W, Gonsior S J, Markham D A, et al. Environ. Sci. Technol., 2006, 40 : 5395 5401 [92 ] Sinkkonen S, Rantalainen A L, Paasivirta J, et al. Chemosphere, 2004, 56 : 767 775 [93 ] Hiebl J, Vetter W. J. Agr. Food Chem., 2007, 55 : 3319 3324 [94 ] Jan k K, Sellstrgm U, Johansson A K, et al. Chemosphere, 2008, 73 : S193 S200 [95 ] Tomy G T, Budarkowski W, Halldorson T, et al. Environ. Sci. Technol., 2004b, 38 : 2298 2303 [96 ] Janak K, Covaci A, Voorspoels S, et al. Environ. Sci. Technol., 2005, 39 : 1987 1994 [97 ] Abdallaha M A E, Ibarra C, Neels H, et al. J. Chromatogr. A, 2008, 1190 : 333 341 [98 ] Barontini F, Cozzani V, Petarca L. Ind. Eng. Chem. Res., 2001, 40 : 3270 3280 [99 ] Eriksson J, Rahm S, Green N, et al. Chemosphere, 2004, 54 : 117 126 [100 ] Marsanich K, Zanelli S, Barontini F, et al. Thermochim. Acta, 2004, 421 : 95 103 [101 ] Barontini F, Cozzani V, Marsanich K, et al. J. Anal. Appl. Pyrolysis, 2004, 72 : 41 53 [102 ] Ronen Z, Abelovich A. Appl. Environ. Microbiol., 2000, 66 : 2372 2377 [103 ] Arbeli Z, Ronen Z. Biodegradation, 2003, 14 : 385 395 [104 ] Arbeli Z, Ronen Z, D az2b ez M C. Chemosphere, 2006, 64 : 1472 1478 [105 ] Watanabe I, Kashimoto T, Tatsukawa R. Bull Environ. Contam. Toxicol., 1983, 31 : 48 52 [106 ] Ravit B, Ehrenfeld J G, H ggblom M M. Soil Biol. Biochem., 2005, 37 : 1049 1057 [107 ] Schauer U M D, Vglkel W, Dekant W. Toxicol. Sci., 2006, 91 : 49 58 [108 ] Kuester R K, S lyom A M, Rodriguez V R, et al. Toxicol. Sci., 2007, 96 : 237 245 [109 ] Szyma ska J A, Sapota A, Frydrych B. Chemosphere, 2000, 45 : 693 700 [110 ] Chignell C F, Han S K, Mouithys2Mickalad A, et al. Toxicol. Appl. Pharmacol., 2008, 230 : 17 22 [111 ] Hakk H, Larsen G, Bergman!, et al. Xenobiotica, 2000, 30 : 881 890