52. Macherius A, Seiwert B, Schröder P, Huber C, Lorenz WRT (2014) Identification of plant
metabolites of environmental contaminants by UPLC-QToF-MS: the in vitro metabolism of
triclosan in horseradish. J Agric Food Chem 62:1001–1009
53. Nehlig A (2018) Interindividual differences in caffeine metabolism and factors driving
caffeine consumption. Pharmacol Rev 70:384–411. https://doi.org/10.1124/pr.117.014407
54. Van Eerd LL, Hoagland RE, Zablotowicz RM, Hall JC (2003) Pesticide metabolism in plants
and microorganisms. Weed Sci 51:472–495. https://doi.org/10.1614/0043-1745(2003)051[
0472:pmipam]2.0.co;2
55. Levsen K, Schiebel HM, Behnke B et al (2005) Structure elucidation of phase II metabolites
by tandem mass spectrometry: an overview. J Chromatogr A 1067:55–72. https://doi.org/10.
1016/j.chroma.2004.08.165
56. Pérez S, Farkas M, Barceló D, Aga DS (2007) Characterization of glutathione conjugates of
chloroacetanilide pesticides using ultra-performance liquid chromatography/quadrupole timeof-flight mass spectrometry and liquid chromatography/ion trap mass spectrometry. Rapid
Commun Mass Spectrom 21:4017–4022. https://doi.org/10.1002/rcm
57. Bártíková H, Skálová L, Stuchĺková L et al (2015) Xenobiotic-metabolizing enzymes in plants
and their role in uptake and biotransformation of veterinary drugs in the environment. Drug
Metab Rev 47:374–387. https://doi.org/10.3109/03602532.2015.1076437
58. Macherius A, Eggen T, Lorenz W et al (2012) Metabolization of the bacteriostatic agent
triclosan in edible plants and its consequences for plant uptake assessment. Environ Sci
Technol 46:10797–10804. https://doi.org/10.1021/es3028378
59. Schmitt R, Kaul J, Trenck TVD et al (1985) β-d-Glucosyl and O-malonyl-β-d-glucosyl
conjugates of pentachlorophenol in soybean and wheat: identification and enzymatic synthesis. Pestic Biochem Physiol 24:77–85. https://doi.org/10.1016/0048-3575(85)90116-6
60. Chen F, Huber C, Schröder P (2017) Fate of the sunscreen compound oxybenzone in Cyperus
alternifolius based hydroponic culture: uptake, biotransformation and phytotoxicity.
Chemosphere 182:638–646. https://doi.org/10.1016/j.chemosphere.2017.05.072
61. Chen F, Huber C, May R, Schröder P (2016) Metabolism of oxybenzone in a hairy root
culture: perspectives for phytoremediation of a widely used sunscreen agent. J Hazard Mater
306:230–236. https://doi.org/10.1016/j.jhazmat.2015.12.022
62. Rea PA (2007) Plant ATP-binding cassette transporters. Annu Rev Plant Biol 58:347–375.
https://doi.org/10.1146/annurev.arplant.57.032905.105406
63. Windsor B, Roux S, Lloy A (2003) Multiherbicide tolerance conferred by AtPgp1 and apyrase
overexpression in Arabidopsis thaliana. Nat Biotechnol 21:428–433
64. Sandermann Jr H (1987) Pestizid-Rückstände in Nahrungspflanzen. Die Rolle des pflanzlichen
Metabolismus. Naturwissenschaften 74:573–578
65. Matern U, Heller W, Himmelspach K (1983) Conformational changes of apigenin 7-O-(6-Omalonylglucoside), a vacuolar pigment from parsley, with solvent composition and proton
concentration. Eur J Biochem 133:439–448
66. Lao S, Loutre C, Brazier M et al (2003) 3, 4-Dichloroaniline is detoxified and exported via
different pathways in Arabidopsis and soybean. Phytochemistry 63:653–661
67. Brazier-Hicks M, Evans KM, Cunningham OD et al (2008) Catabolism of glutathione
conjugates in Arabidopsis thaliana – role in metabolic reactivation of the herbicide safener
fenclorim. J Biol Chem 283:21102–21112
68. Bouzayen M, Latché A, Pech JCMG (1989) Carrier-mediated uptakeof 1-(malonylamino)
cyclopropane-1-carboxylic acid in vacuoles isolated from Catharanthus roseus cells. Plant
Phys 91:1317–1322
69. Tophof S, Martinoia E, Kaiser G, Hartung W, Amrhein N (1989) Compartmentation and
transport of 1-aminocyclopropane-1-carboxylic acidand N-malonyl-1-aminocyclopropane-1carboxylic acid in barley andwheat mesophyll cells and protoplasts. Phys Plant 75:333–339
70. Coleman JOD, Blake-Kalff MMA, Davies TGE (1997) Detoxification of xenobiotics by
plants: chemical modification and vacuolar compartmentation. Trends Plant Sci 2:144–151.
https://doi.org/10.1016/S1360-1385(97)01019-4
260
A. Sauvêtre et al.
metabolites of environmental contaminants by UPLC-QToF-MS: the in vitro metabolism of
triclosan in horseradish. J Agric Food Chem 62:1001–1009
53. Nehlig A (2018) Interindividual differences in caffeine metabolism and factors driving
caffeine consumption. Pharmacol Rev 70:384–411. https://doi.org/10.1124/pr.117.014407
54. Van Eerd LL, Hoagland RE, Zablotowicz RM, Hall JC (2003) Pesticide metabolism in plants
and microorganisms. Weed Sci 51:472–495. https://doi.org/10.1614/0043-1745(2003)051[
0472:pmipam]2.0.co;2
55. Levsen K, Schiebel HM, Behnke B et al (2005) Structure elucidation of phase II metabolites
by tandem mass spectrometry: an overview. J Chromatogr A 1067:55–72. https://doi.org/10.
1016/j.chroma.2004.08.165
56. Pérez S, Farkas M, Barceló D, Aga DS (2007) Characterization of glutathione conjugates of
chloroacetanilide pesticides using ultra-performance liquid chromatography/quadrupole timeof-flight mass spectrometry and liquid chromatography/ion trap mass spectrometry. Rapid
Commun Mass Spectrom 21:4017–4022. https://doi.org/10.1002/rcm
57. Bártíková H, Skálová L, Stuchĺková L et al (2015) Xenobiotic-metabolizing enzymes in plants
and their role in uptake and biotransformation of veterinary drugs in the environment. Drug
Metab Rev 47:374–387. https://doi.org/10.3109/03602532.2015.1076437
58. Macherius A, Eggen T, Lorenz W et al (2012) Metabolization of the bacteriostatic agent
triclosan in edible plants and its consequences for plant uptake assessment. Environ Sci
Technol 46:10797–10804. https://doi.org/10.1021/es3028378
59. Schmitt R, Kaul J, Trenck TVD et al (1985) β-d-Glucosyl and O-malonyl-β-d-glucosyl
conjugates of pentachlorophenol in soybean and wheat: identification and enzymatic synthesis. Pestic Biochem Physiol 24:77–85. https://doi.org/10.1016/0048-3575(85)90116-6
60. Chen F, Huber C, Schröder P (2017) Fate of the sunscreen compound oxybenzone in Cyperus
alternifolius based hydroponic culture: uptake, biotransformation and phytotoxicity.
Chemosphere 182:638–646. https://doi.org/10.1016/j.chemosphere.2017.05.072
61. Chen F, Huber C, May R, Schröder P (2016) Metabolism of oxybenzone in a hairy root
culture: perspectives for phytoremediation of a widely used sunscreen agent. J Hazard Mater
306:230–236. https://doi.org/10.1016/j.jhazmat.2015.12.022
62. Rea PA (2007) Plant ATP-binding cassette transporters. Annu Rev Plant Biol 58:347–375.
https://doi.org/10.1146/annurev.arplant.57.032905.105406
63. Windsor B, Roux S, Lloy A (2003) Multiherbicide tolerance conferred by AtPgp1 and apyrase
overexpression in Arabidopsis thaliana. Nat Biotechnol 21:428–433
64. Sandermann Jr H (1987) Pestizid-Rückstände in Nahrungspflanzen. Die Rolle des pflanzlichen
Metabolismus. Naturwissenschaften 74:573–578
65. Matern U, Heller W, Himmelspach K (1983) Conformational changes of apigenin 7-O-(6-Omalonylglucoside), a vacuolar pigment from parsley, with solvent composition and proton
concentration. Eur J Biochem 133:439–448
66. Lao S, Loutre C, Brazier M et al (2003) 3, 4-Dichloroaniline is detoxified and exported via
different pathways in Arabidopsis and soybean. Phytochemistry 63:653–661
67. Brazier-Hicks M, Evans KM, Cunningham OD et al (2008) Catabolism of glutathione
conjugates in Arabidopsis thaliana – role in metabolic reactivation of the herbicide safener
fenclorim. J Biol Chem 283:21102–21112
68. Bouzayen M, Latché A, Pech JCMG (1989) Carrier-mediated uptakeof 1-(malonylamino)
cyclopropane-1-carboxylic acid in vacuoles isolated from Catharanthus roseus cells. Plant
Phys 91:1317–1322
69. Tophof S, Martinoia E, Kaiser G, Hartung W, Amrhein N (1989) Compartmentation and
transport of 1-aminocyclopropane-1-carboxylic acidand N-malonyl-1-aminocyclopropane-1carboxylic acid in barley andwheat mesophyll cells and protoplasts. Phys Plant 75:333–339
70. Coleman JOD, Blake-Kalff MMA, Davies TGE (1997) Detoxification of xenobiotics by
plants: chemical modification and vacuolar compartmentation. Trends Plant Sci 2:144–151.
https://doi.org/10.1016/S1360-1385(97)01019-4
260
A. Sauvêtre et al.